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21 article(s) from Jones, Peter G

Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes

Grzegorz Mlostoń,
Mateusz Kowalczyk,
André U. Augustin,
Peter G. Jones and
Daniel B. Werz

Full Research Paper
Published 10 Jun 2020

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1. Graphical Abstract
2. Scheme 1: Synthesis of spirotetrahydrothiophenes 3 via non-concerted [3 + 2]-cycloadditions of thiocarbonyl y...
  
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3. Scheme 2: Formal [3 + 2]-cycloadditions of thioketones and [4 + 3]-cycloadditions of thiochalcones with donor...
  
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4. Scheme 3: Formal [3 + 2]-cycloadditions of dimethyl 2-substituted cyclopropane-1,1-dicarboxylates 5a–g with f...
  
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5. Figure 1: Thermal ellipsoid plots of the molecular structures of cis-9c and trans-9d drawn using 50% probabil...
  
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6. Scheme 4: Plausible mechanism for the formal [3 + 2]-cycloadditions of ferrocenyl thioketones 8 with D–A cycl...
  
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Beilstein J. Org. Chem. 2020, 16, 1288–1295, doi:10.3762/bjoc.16.109

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Synthesis of eunicellane-type bicycles embedding a 1,3-cyclohexadiene moiety

Alex Frichert,
Peter G. Jones and
Thomas Lindel

Full Research Paper
Published 20 Sep 2018

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1. Graphical Abstract
2. Figure 1: Bicyclic eunicellane-type diterpenes.
  
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3. Figure 2: Synthetic eunicellane-type compounds with benzene partial structure.
  
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4. Scheme 1: Access to ketoester 14 that did not cyclize to the ethyl vinyl ether under McMurry conditions.
  
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5. Scheme 2: Synthesis of the 1,3-cyclohexadiene-containing eunicellane-type [8.4.0]bicycle 18 by McMurry coupli...
  
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6. Figure 3: Preferred conformations of diastereomeric diols 18 and 19 including decisive NOESY correlations.
  
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7. Scheme 3: Assembly of the envisaged cyclization precursor 27.
  
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8. Scheme 4: Structure analysis of diastereomeric cyanohydrins 29 and 30.
  
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9. Scheme 5: Formation of allenes 32 and 34 from sterically crowded propargylic alcohol 31.
  
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Beilstein J. Org. Chem. 2018, 14, 2461–2467, doi:10.3762/bjoc.14.222

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Antibacterial structure–activity relationship studies of several tricyclic sulfur-containing flavonoids

Lucian G. Bahrin,
Henning Hopf,
Peter G. Jones,
Laura G. Sarbu,
Cornelia Babii,
Alina C. Mihai,
Marius Stefan and
Lucian M. Birsa

Full Research Paper
Published 23 May 2016

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1. Graphical Abstract
2. Figure 1: The molecular structure of tricyclic flavonoid 1.
  
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3. Scheme 1: Synthesis of flavanones 4a–m and tricyclic flavonoids 5a–m. Conditions: i) EtOH, reflux, 4 h; ii) H₂...
  
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4. Figure 2: The syn and anti-isomers of flavanones 4.
  
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5. Figure 3: Molecular structures of 4d (left) and 4f (right). Ellipsoids represent 50% probability levels [24].
  
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6. Figure 4: Molecular structure of 5a (left, both independent molecules) and 5b (right, one of two independent ...
  
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Beilstein J. Org. Chem. 2016, 12, 1065–1071, doi:10.3762/bjoc.12.100

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[2.2]Paracyclophane derivatives containing tetrathiafulvalene moieties

Laura G. Sarbu,
Lucian G. Bahrin,
Peter G. Jones,
Lucian M. Birsa and
Henning Hopf

Letter
Published 15 Oct 2015

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1. Graphical Abstract
2. Scheme 1: Synthesis of 2-N,N-dialkylamino-4-([2.2]paracyclophan-4-yl)-1,3-dithiol-2-ylium perchlorates 5.
  
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3. Figure 1: Molecular structure of compound 4a. Ellipsoids represent 30% probability levels. Selected molecular...
  
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4. Scheme 2: Synthesis of tetrathiafulvalenes 7.
  
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5. Figure 2: Molecular structure of compound 6 (two independent molecules). Ellipsoids represent 30% probability...
  
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Beilstein J. Org. Chem. 2015, 11, 1917–1921, doi:10.3762/bjoc.11.207

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SmI₂-mediated dimerization of indolylbutenones and synthesis of the myxobacterial natural product indiacen B

Nils Marsch,
Peter G. Jones and
Thomas Lindel

Full Research Paper
Published 21 Sep 2015

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1. Graphical Abstract
2. Figure 1: Prenylated indole alkaloids raputindole A from the rutaceous tree Raputia simulans and indiacen B f...
  
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3. Scheme 1: Synthesis and SmI₂-mediated reductive dimerization of natural product 5.
  
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4. Scheme 2: Model visualizing the stereochemical course of the cyclopentanol formation leading to product 6. Po...
  
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5. Scheme 3: Meyer–Schuster rearrangement of 13 and SmI₂-mediated reductive [3 + 2] cycloaddition, followed by e...
  
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6. Scheme 4: Nazarov-type cyclization of 14 to cyclopentanones 17 and 18; synthesis of verticillatine B (20).
  
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7. Scheme 5: Synthesis and X-ray analysis of indiacen B (2, ORTEP drawing with ellipsoides at 50% probability).
  
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Beilstein J. Org. Chem. 2015, 11, 1700–1706, doi:10.3762/bjoc.11.184

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The chemical behavior of terminally tert-butylated polyolefins

Dagmar Klein,
Henning Hopf,
Peter G. Jones,
Ina Dix and
Ralf Hänel

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Published 24 Jul 2015

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1. Graphical Abstract
2. Scheme 1: The polyenes 2 stabilized by terminal tert-butyl substituents.
  
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3. Scheme 2: The catalytic hydrogenation of diene 3.
  
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4. Figure 1: The structure of compound 4 in the crystal. Ellipsoids correspond to 30% probability levels.
  
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5. Scheme 3: The catalytic hydrogenation of triene 7.
  
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6. Scheme 4: Addition of bromine to model dienes.
  
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7. Scheme 5: Bromine addition to diene 3 and triene 7.
  
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8. Scheme 6: Bromine addition to the higher oligoenes 19–22.
  
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9. Figure 2: (a) The structure of compound 24 in the crystal. Ellipsoids correspond to 50% probability levels. (...
  
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10. Figure 3: The structure of compound 25 in the crystal. This was a structure of poor quality and served only t...
  
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11. Scheme 7: Epoxidation of triene 7 with MCPBA and DMDO.
  
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12. Scheme 8: Epoxidation of tetraene 19 with MCPBA and DMDO.
  
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13. Scheme 9: Diels–Alder addition of PTAD (36) to triene 7 and tetraene 19.
  
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14. Figure 4: The structure of compound 37 in the crystal. Only one of two independent molecules is shown. Ellips...
  
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15. Scheme 10: Diels-Alder addition of oligoenes 20 and 21 with PTAD (36).
  
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16. Scheme 11: Addition of excess PTAD (36) to hexaene 21 and heptaene 22.
  
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17. Scheme 12: TCNE addition to oligoolefins: from tetraene 19 to nonaene 42.
  
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18. Figure 5: The structure of compound 43 in the crystal. Only one of two independent molecules is shown. Ellips...
  
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19. Scheme 13: Photochemical experiments with tetraene 19.
  
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20. Figure 6: The structure of compound 52 in the crystal. Ellipsoids correspond to 50% probability levels.
  
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Beilstein J. Org. Chem. 2015, 11, 1246–1258, doi:10.3762/bjoc.11.139

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The preparation of new functionalized [2.2]paracyclophane derivatives with N-containing functional groups

Henning Hopf,
Swaminathan Vijay Narayanan and
Peter G. Jones

Full Research Paper
Published 07 Apr 2015

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1. Graphical Abstract
2. Figure 1: A selection of highly substituted/functionalized [2.2]paracyclophanes.
  
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3. Figure 2: A selection of [2.2]paracyclophanes carrying several nitrogen-containing substituents.
  
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4. Scheme 1: The preparation of 4,12-diamino[2.2]paracyclophane (8).
  
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5. Scheme 2: Preparation of cyclic and acyclic urethanes from 4,12-diisocyanato[2.2]paracyclophane (16).
  
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6. Figure 3: (a, above): The molecule of compound 18 in the crystal; ellipsoids represent 50% probability levels...
  
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7. Scheme 3: LiAlH₄-reduction of crownophane 18.
  
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8. Figure 4: (a, above): The molecule of compound 22 in the crystal; ellipsoids represent 30% probability levels...
  
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9. Scheme 4: The preparation of several derivatives of 4,16-dicarboxy[2.2]paracyclophane (25) carrying N-contain...
  
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10. Figure 5: The molecule of compound 26 in the crystal; ellipsoids represent 50% probability levels. Only the a...
  
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11. Figure 6: (a, above): The molecule of compound 28 in the crystal; ellipsoids represent 50% probability levels...
  
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Beilstein J. Org. Chem. 2015, 11, 437–445, doi:10.3762/bjoc.11.50

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Attempts to prepare an all-carbon indigoid system

Şeref Yildizhan,
Henning Hopf and
Peter G. Jones

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Published 18 Mar 2015

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1. Graphical Abstract
2. Scheme 1: From indigo to heteroindigo derivatives and all-carbon-indigo.
  
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3. Scheme 2: Attempts to prepare the α-methylene ketones 12 and 13.
  
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4. Figure 1: a) Both independent molecules of compound 13 in the crystal; ellipsoids represent 50% probability l...
  
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5. Scheme 3: Dimerization of 13 under McMurry conditions.
  
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6. Figure 2: a) The molecule of compound 17 in the crystal; ellipsoids represent 50% probability levels. Only th...
  
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7. Scheme 4: Dimerization of indan-1-one (18) by a stepwise approach.
  
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8. Scheme 5: Methylenation of 19 and bisalkylation of the product 23 with 1,2-dibromoethane.
  
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9. Figure 3: The molecule of compound 23 in the crystal. Ellipsoids represent 50% probability levels. Only the a...
  
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10. Figure 4: a) The molecule of compound 24 in the crystal. Ellipsoids represent 50% probability levels. Only th...
  
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11. Figure 5: One of the two independent molecules of compound 25 in the crystal. Ellipsoids represent 50% probab...
  
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12. Scheme 6: Cross-conjugated hydrocarbons by Thiele condensation.
  
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13. Figure 6: a) The molecule of compound 30 in the crystal. Ellipsoids represent 50% probability levels. Only th...
  
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Beilstein J. Org. Chem. 2015, 11, 363–372, doi:10.3762/bjoc.11.42

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Selenium halide-induced bridge formation in [2.2]paracyclophanes

Laura G. Sarbu,
Henning Hopf,
Peter G. Jones and
Lucian M. Birsa

Full Research Paper
Published 31 Oct 2014

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1. Graphical Abstract
2. Scheme 1: Reactions of selenium dichloride and selenium dibromide with pseudo-geminal bis(acetylene) 1.
  
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3. Scheme 2: Reaction of phenylselenyl chloride with pseudo-geminal bis(acetylene) 1.
  
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4. Scheme 3: Plausible reaction mechanism for the addition of phenylselenyl chloride to pseudo-geminal bis(acety...
  
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5. Scheme 4: Reactions of selenium dichloride and selenium dibromide with 4,13-bis(propyn-1-yl)[2.2]paracyclopha...
  
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6. Figure 1: Molecular structure of compound 13. Ellipsoids represent 50% probability levels. Selected molecular...
  
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Beilstein J. Org. Chem. 2014, 10, 2550–2555, doi:10.3762/bjoc.10.266

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Five-membered ring annelation in [2.2]paracyclophanes by aldol condensation

Henning Hopf,
Swaminathan Vijay Narayanan and
Peter G. Jones

Full Research Paper
Published 28 Aug 2014

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1. Graphical Abstract
2. Scheme 1: [2.2]Paracyclophane derivatives with annelated alicyclic rings.
  
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3. Scheme 2: The formation of the tetraketone 9 by a Diels–Alder addition.
  
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4. Scheme 3: The possible structures of the aldols formed from 9.
  
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5. Figure 1: Structure of 12·CDCl₃ in the crystal. Ellipsoids represent 50% probability levels. Selected bond le...
  
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6. Scheme 4: The mechanism of the aldol cyclization.
  
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7. Scheme 5: Dehydration of the aldol 12.
  
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8. Scheme 6: Dehydration of the aldol 15.
  
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9. Figure 2: Structure of compound 21 in the crystal. Ellipsoids represent 50% probability levels. Selected bond...
  
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Beilstein J. Org. Chem. 2014, 10, 2021–2026, doi:10.3762/bjoc.10.210

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Building complex carbon skeletons with ethynyl[2.2]paracyclophanes

Ina Dix,
Lidija Bondarenko,
Peter G. Jones,
Thomas Oeser and
Henning Hopf

Full Research Paper
Published 27 Aug 2014

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1. Graphical Abstract
2. Scheme 1: Planar and layered ethynyl aromatics as building blocks for extended aromatic structures.
  
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3. Scheme 2: Previous coupling experiments with pseudo-ortho-diethynyl[2.2]paracyclophane 4.
  
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4. Scheme 3: Glaser coupling of pseudo-gem-diethynyl[2.2]paracyclophane 2.
  
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5. Scheme 4: Glaser coupling of pseudo-ortho-diethynyl[2.2]paracyclophane, 4.
  
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6. Figure 1: Above: The molecule of compound 11 in the crystal; ellipsoids represent 30% probability levels. Onl...
  
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7. Figure 2: Above: The molecule of compound 12 in the crystal; ellipsoids represent 50% probability levels. Onl...
  
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8. Scheme 5: Sonogashira coupling of aldehyde 13 with ortho-diiodobenzene (14).
  
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9. Scheme 6: Preparation of benzologs of dimers 11/12.
  
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10. Figure 3: Above: The molecule of compound 19 in the crystal; ellipsoids represent 50% probability levels. Sol...
  
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11. Figure 4: Above: One of the three independent molecules of compound 20 in the crystal; ellipsoids represent 3...
  
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12. Scheme 7: Cross dimerization of 1 and 4.
  
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13. Figure 5: The molecule of compound 22 in the crystal; ellipsoids represent 50% probability levels.
  
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14. Scheme 8: An attempt to prepare a biphenylenophane.
  
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15. Figure 6: The molecule of compound 26 in the crystal; ellipsoids represent 50% probability levels.
  
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Beilstein J. Org. Chem. 2014, 10, 2013–2020, doi:10.3762/bjoc.10.209

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A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones

Jubi John,
Eliza Târcoveanu,
Peter G. Jones and
Henning Hopf

Full Research Paper
Published 27 Jun 2014

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1. Graphical Abstract
2. Figure 1: Bioactive molecules I [19], II [26], III & IV [21,22] with 3(2H)-furanone moiety.
  
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3. Scheme 1: Pd-catalyzed synthesis of 3(2H)-furanones from activated alkenes [40].
  
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4. Scheme 2: Pd-catalyzed synthesis of 3(2H)-furanone from tosylimine 1a.
  
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5. Figure 2: Generalisation with aromatic and aliphatic imines (reaction conditions: 1 (1.0 equiv), 2 (1.1 equiv...
  
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6. Figure 3: Thermal ellipsoid diagrams (50% probability levels) of 4-substituted-3(2H)-furanones 7 (above) and ...
  
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7. Scheme 3: Mechanism of formation of the 3(2H)-furanone derivative from an imine.
  
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8. Scheme 4: Pd-catalyzed synthesis of 3(2H)-furanone from diazoester 19a.
  
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9. Figure 4: Generalisation with diazo esters (reaction conditions: 19 (1.0 equiv), 2 (1.1 equiv), Pd(PPh₃)₄ (5 ...
  
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10. Scheme 5: Synthesis of aza-prostaglandin analogue.
  
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Beilstein J. Org. Chem. 2014, 10, 1462–1470, doi:10.3762/bjoc.10.150

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Total synthesis and cytotoxicity of the marine natural product malevamide D and a photoreactive analog

Werner Telle,
Gerhard Kelter,
Heinz-Herbert Fiebig,
Peter G. Jones and
Thomas Lindel

Full Research Paper
Published 03 Feb 2014

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1. Graphical Abstract
2. Figure 1: Structures of the strongly cytotoxic marine natural products malevamide D (1), isodolastatin H (2),...
  
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3. Scheme 1: Total synthesis of malevamide D (1). a) DMSO (16 equiv), NEt₃ (5 equiv), pyridine·SO₃ (5 equiv), 0 ...
  
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4. Scheme 2: Formation of oxazolylphosphate 18 on attempted DEPC-mediated coupling of dipeptide 15.
  
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5. Scheme 3: Synthesis of tosyloximes (Z)-22 and (E)-22, X-ray structure of (E)-22. a) NH₂OH·HCl (1.5 equiv), py...
  
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6. Scheme 4: Synthesis of photo malevamide D 30. a) NH₃(l), t-BuOMe, −40 °C, 2 h, rt, 16 h, quant. b) I₂ (1.2 eq...
  
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7. Figure 2: DSC curve of diazirine 25, heating rate 5 °C/min.
  
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Beilstein J. Org. Chem. 2014, 10, 316–322, doi:10.3762/bjoc.10.29

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Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

Catalin V. Maftei,
Elena Fodor,
Peter G. Jones,
M. Heiko Franz,
Gerhard Kelter,
Heiner Fiebig and
Ion Neda

Full Research Paper
Published 25 Oct 2013

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1. Graphical Abstract
2. Figure 1: Natural products having a 1,2,4-oxadiazole core.
  
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3. Figure 2: Examples of 1,2,4-oxadiazole antitumorals.
  
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4. Scheme 1: Common synthetic strategies toward 1,2,4-oxadiazoles; (a) amidoxime route; (b) 1,3 dipolar cycloadd...
  
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5. Scheme 2: One-pot synthesis of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) by using the amidoxime route....
  
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6. Figure 3: Molecular structure of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1). Atoms are drawn as 50% the...
  
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7. Figure 4: Packing diagram of compound 1. Hydrogen bonds are indicated as dashed lines.
  
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8. Scheme 3: One-pot synthesis of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) by using the 1,3-dipolar cycl...
  
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9. Figure 5: Molecular structure of 3-tert-butyl-5-(4-nitrophenyl)-1,2,4-oxadiazole (2). Atoms are drawn as 50% ...
  
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10. Figure 6: Packing diagram of compound (2) showing C–H···O interactions.
  
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11. Scheme 4: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4).
  
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12. Figure 7: Molecular structure of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4). At...
  
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13. Figure 8: Molecular structure of 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4 oxobutanoate (5). Ato...
  
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14. Figure 9: Packing diagram of compound (5). Dashed lines indicate hydrogen bonds.
  
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15. Scheme 5: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7).
  
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16. Figure 10: Molecular structure of (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic ac...
  
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17. Figure 11: Packing diagram of compound 6. Dashed lines indicate hydrogen bonds.
  
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18. Figure 12: In vitro antitumor activity of compounds 1, 3–7 toward 11 human tumor cell lines.
  
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19. Figure 13: Individual IC₅₀ values [µM] of compounds 1, 3–7 in a panel of 11 human tumor cell lines.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2202–2215, doi:10.3762/bjoc.9.259

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The preparation of several 1,2,3,4,5-functionalized cyclopentane derivatives

André S. Kelch,
Peter G. Jones,
Ina Dix and
Henning Hopf

Full Research Paper
Published 19 Aug 2013

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1. Graphical Abstract
2. Scheme 1: The first members of the [n]radialene series and retrosynthesis for [5]radialene (3).
  
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3. Scheme 2: Preparation of cis,cis,cis,cis-1,2,3,4,5-pentakis(hydroxymethyl)cyclopentane (16) according to Tolb...
  
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4. Scheme 3: The preparation of derivatives of 16 better suited for nucleophilic substitution and elimination.
  
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5. Figure 1: Structure of 19 in the crystal; ellipsoids represent 50% probability levels.
  
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6. Scheme 4: Preparation of the pentaacetate 21 from 16.
  
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7. Scheme 5: Preparation of the cycloheptadiene octaesters 24/25 according to Diels [11] and Le Goff [13], respectively,...
  
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8. Figure 2: Structure of 24 in the crystal; ellipsoids represent 30% probability levels.
  
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9. Figure 3: Structure of 26 in the crystal; ellipsoids represent 30% probability levels.
  
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10. Scheme 6: Derivatives derived from the pentaester mixture 26/27.
  
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11. Scheme 7: Bromination of 1,2,3,4,5-pentamethylcyclopenta-1,3-diene (8).
  
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12. Figure 4: Structure of 32 in the crystal; ellipsoids represent 50% probability levels.
  
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Beilstein J. Org. Chem. 2013, 9, 1705–1712, doi:10.3762/bjoc.9.195

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Tricyclic flavonoids with 1,3-dithiolium substructure

Lucian G. Bahrin,
Peter G. Jones and
Henning Hopf

Full Research Paper
Published 16 Nov 2012

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1. Graphical Abstract
2. Figure 1: Polycyclic flavonoids.
  
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3. Scheme 1: The synthesis of flavonoids 6 and 7.
  
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4. Figure 2: Diastereoisomers of flavonoids 6.
  
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5. Figure 3: Molecular structure of flavonoid 6a in the solid state. Ellipsoids represent 50% probability levels...
  
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6. Figure 4: Molecular structure of flavonoid 6b in the solid state. Ellipsoids represent 50% probability levels...
  
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7. Figure 5: Molecular structure of flavonoid 7a in the solid state. Ellipsoids represent 50% probability levels....
  
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Beilstein J. Org. Chem. 2012, 8, 1999–2003, doi:10.3762/bjoc.8.226

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Synthesis of new pyrrole–pyridine-based ligands using an in situ Suzuki coupling method

Matthias Böttger,
Björn Wiegmann,
Steffen Schaumburg,
Peter G. Jones,
Wolfgang Kowalsky and
Hans-Hermann Johannes

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Published 09 Jul 2012

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1. Graphical Abstract
2. Scheme 1: β-diketonate complexes (left), homoleptic complexes (middle) and planned homoleptic complexes of eu...
  
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3. Scheme 2: Pyrrole–pyridine-based structures synthesized in this study.
  
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4. Scheme 3: Retrosynthetic approach for structures 1–3.
  
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5. Scheme 4: Synthesis of the heteroaryl bromides used in the coupling reaction.
  
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6. Scheme 5: Generation of the borate intermediate 21/22.
  
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7. Scheme 6: In situ Suzuki coupling reactions of the heteroaryl bromides 8–10.
  
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8. Figure 1: The structure of compound 1 in the crystal. Ellipsoids correspond to 50% probability levels.
  
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9. Figure 2: Packing diagram of compound 1, viewed parallel to the y-axis in the range y ≈ 1/4. Hydrogen bonds a...
  
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10. Figure 3: The structure of compound 2·CH₃OH in the crystal. Ellipsoids correspond to 50% probability levels. ...
  
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11. Figure 4: Packing diagram of compound 2·CH₃OH showing the formation of inversion-symmetric "stacked" dimers. ...
  
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12. Figure 5: The structure of compound 3·C₂H₅OH in the crystal. Ellipsoids correspond to 50% probability levels....
  
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13. Figure 6: Packing diagram of compound 3·C₂H₅OH. Hydrogen bonds are shown as thick dashed lines. Hydrogen atom...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2012, 8, 1037–1047, doi:10.3762/bjoc.8.116

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Intraannular photoreactions in pseudo-geminally substituted [2.2]paracyclophanes

Henning Hopf,
Vitaly Raev and
Peter G. Jones

Full Research Paper
Published 24 May 2011

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1. Graphical Abstract
2. Scheme 1: [2.2]Paracyclophanes as scaffolds for intraannular photodimerization reactions in solution.
  
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3. Scheme 2: Stereospecific intramolecular [2+2]photoadditions using [2.2]paracyclophane spacers.
  
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4. Scheme 3: Different conformations of pseudo-geminal divinyl[2.2]paracyclophane.
  
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5. Scheme 4: Preparation of tetraene 11.
  
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6. Scheme 5: Photolysis of tetraene 11.
  
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7. Figure 1: The molecule of compound 13 in the crystal. Ellipsoids correspond to 30% probability levels.
  
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8. Scheme 6: Photolysis of trans,trans-dienal 10.
  
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9. Figure 2: The molecule of compound 15 in the crystal. Ellipsoids correspond to 30% probability levels.
  
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10. Scheme 7: Cis–trans-isomerizations of the double bonds of the pseudo-geminal cyclophanes 11 and 19.
  
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11. Scheme 8: Preparation of the vinylcyclopropanes 22–24.
  
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12. Figure 3: The two independent molecules of compound Z,Z-22 in the crystal. Ellipsoids correspond to 50% proba...
  
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13. Figure 4: The molecule of compound 23 in the crystal. Ellipsoids correspond to 50% probability levels.
  
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14. Figure 5: The molecule of compound 24 in the crystal. Ellipsoids correspond to 30% probability levels.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2011, 7, 658–667, doi:10.3762/bjoc.7.78

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A surprising new route to 4-nitro-3-phenylisoxazole

Henning Hopf,
Aboul-fetouh E. Mourad and
Peter G. Jones

Preliminary Communication
Published 23 Jun 2010

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1. Graphical Abstract
2. Scheme 1: Preparation of 2 and 4 by treatment of cinnamyl alcohol (1).
  
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3. Figure 1: The crystal structure of compound 4. Ellipsoids correspond to 50% probability levels.
  
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4. Figure 2: Packing diagram of compound 4 viewed perpendicular to (101). Hydrogen bonds are indicated by thick ...
  
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5. Scheme 2: Suggested mechanism for the formation of 4.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2010, 6, No. 68, doi:10.3762/bjoc.6.68

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A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions

Marc Debeaux,
Kai Brandhorst,
Peter G. Jones,
Henning Hopf,
Jörg Grunenberg,
Wolfgang Kowalsky and
Hans-Hermann Johannes

Full Research Paper
Published 16 Jun 2009

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1. Graphical Abstract
2. Scheme 1: Behaviour of benzanthrone (1) towards phenylmagnesium chloride (a), phenyl lithium (b), and bipheny...
  
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3. Figure 1: ¹H NMR spectra (200 MHz) of 4 in CDCl₃ solution and time dependence.
  
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4. Scheme 2: Proposed mechanism for the formation of 4 and its oxidation to 7.
  
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5. Scheme 3: Conversion of the enol 4 under acidic conditions and reaction products.
  
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6. Scheme 4: Proposed mechanism for the formation of spiro compound 11 and bicyclo[4.3.1]decane derivative 12.
  
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7. Scheme 5: Proposed mechanism for the formation of 13.
  
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8. Scheme 6: Proposed mechanism for the formation of 18 as a hydride source and further conversion to 7.
  
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9. Figure 2: Ellipsoid representation (50% level) of compound 7 in the crystal.
  
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10. Figure 3: Packing diagram of compound 7 viewed parallel to b; hydrogen bonds C-H···O are indicated by dashed ...
  
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11. Figure 4: Ellipsoid representation (50% level) of compound 11 in the crystal.
  
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12. Figure 5: Packing diagram of compound 11 viewed perpendicular to the bc plane; hydrogen bonds C-H···π are ind...
  
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13. Figure 6: Ellipsoid representation (50% level) of compound 13 (d₆-DMSO solvate) in the crystal. Hydrogen bond...
  
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14. Figure 7: Packing diagram of compound 13 viewed parallel to c; DMSO molecules (including their hydrogen bonds...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2009, 5, No. 31, doi:10.3762/bjoc.5.31

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Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5)

Henning Hopf,
Christian Beck,
Jean-Pierre Desvergne,
Henri Bouas-Laurent,
Peter G. Jones and
Ludger Ernst

Full Research Paper
Published 07 May 2009

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1. Graphical Abstract
2. Figure 1: Schematic representation of a photochromic system. The reverse reaction can be a photochemical or t...
  
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3. Figure 2: Photochromic reaction of pseudo-gem disubstituted tetraene [2.2]cyclophane 1 in acetonitrile, conc....
  
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4. Figure 3: Molecular structure of 4,13-bis[(1E,3E)-4-(9-anthracenyl)-buta-1,3-dienyl][2.2]paracyclophane (2).
  
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5. Scheme 1: Preparation of 2 (last step), using the Wittig reaction. The preparation of 3 has been described in...
  
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6. Figure 4: Molecular structure of 2 in the crystal. Radii are arbitrary; only selected H atoms are shown.
  
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7. Figure 5: Projection of the molecular structure of 2 exhibiting the closest internuclear distances (distances...
  
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8. Figure 6: Electronic absorption spectra of 2 (conc. ca 10⁻⁴ M) in MCH (full line) and CH₃CN (dotted line) at ...
  
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9. Figure 7: Irradiation of 2 (2.6 × 10⁻⁵ M) in CH₃CN at 400 nm at 20 °C. The spectra were recorded at various t...
  
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10. Figure 8: Irradiation at 306 nm of the photoproduct 4 obtained at 400 nm in the same setup; the spectra were ...
  
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11. Figure 9: Reversibility of the formation of the photoproduct 4 at 400 nm (40 min) and photodissociation of 4 ...
  
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12. Figure 10: ¹H NMR spectra (400 MHz, CDCl3). A: Compound 2, B: Compound 4.
  
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13. Figure 11: Proposed structure of 4 (1,4 : 2′,3′-cycloadduct).
  
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Graphical Abstract

Beilstein J. Org. Chem. 2009, 5, No. 20, doi:10.3762/bjoc.5.20

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