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5 article(s) from Wentrup, Curt

From dipivaloylketene to tetraoxaadamantanes

Gert Kollenz and
Curt Wentrup

Beilstein J. Org. Chem. 2018, 14, 1–10, doi:10.3762/bjoc.14.1

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Scheme 1: Synthetic routes to 2,4,6,8-tetraoxaadamantanes.

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Scheme 2: Conversion of dipivaloylketene (2) to bisdioxines (2,6,9-trioxabicyclo[3.3.1]nona-3,7-dienes) 4 and...

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Scheme 3: 2,6,9-Trioxabicyclo[3.3.1]nonadienes (bisdioxines, 9–13) derived from dipivaloylketene (2).

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Scheme 4: Mechanisms of formation of bisdioxine acid derivatives from dimer 3.

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Scheme 5: Recently reported synthesis of chromenobisdioxines.

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Scheme 6: Formation of tetraoxaadamantanes.

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Scheme 7: Decarboxylative hydrolysis and oxa-Michael-type ring closure.

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Scheme 8: Oxime and hydrazine derivatives of bisdioxines and tetraoxaadamantanes.

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Figure 1: Bistetraoxaadamantane derivatives.

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Scheme 9: Inward-pointing isocyanate, urethane and carbamate groups in bisdioxines. The diisocyanate is obtai...

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Scheme 10: Microwave-assisted tetraoxaadamantane formation.

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Scheme 11: Cyclic bisdioxine ester derivative 34 forming a single mono-tetraoxaadamantane.

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Figure 2: Cyclic bisdioxine derivative not forming a tetraoxaadamantane due to reduced cavity size.

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Figure 3: The bisdioxine-calix[6]arene derivative 37 complexes Cs⁺ but does not form a tetraoxaadamantane der...

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Published 02 Jan 2018

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Molecular cleft or tweezer compounds derived from trioxabicyclo[3.3.1]nonadiene diisocyanate and diacid dichloride

Gert Kollenz,
Ralf Smounig,
Ferdinand Belaj,
David Kvaskoff and
Curt Wentrup

Beilstein J. Org. Chem. 2015, 11, 1–8, doi:10.3762/bjoc.11.1

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Figure 1: 2,6,9-Trioxabicyclo[3.3.1]nonadiene (“bisdioxine”) derivatives.

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Figure 2: B3LYP/6-31G**-calculated structures of the stable endo,endo diisocyanate 1 (left) and the unstable ...

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Scheme 1: Ring opening taking place on attempted optimization of the calculated, putative endo,exo isomer of 1...

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Scheme 2: Synthesis of the di(hexylurea) and di(methyl carbamate) derivatives 4 and 5.

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Figure 3: Stereoscopic ORTEP plot of molecule A of the di(hexylurea) derivative 4 with atomic numbering schem...

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Figure 4: Stereoscopic ORTEP plot of molecule B of 4 with atomic numbering scheme. The ellipsoids are drawn a...

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Figure 5: Stereoscopic ORTEP plot of the di(methyl carbamate) 5 showing the atomic numbering scheme. The elli...

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Figure 6: The lowest-energy calculated structure of 4 (B3LYP/6-31G**; for other conformers and full details s...

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Figure 7: Calculated structure of 5 (B3LYP/6-31G**). Bond lengths are given in Å and angles in degrees. For a...

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Scheme 3: Synthesis of bis-crown ether diamides 7.

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Figure 8: Calculated structure of 7a-a (B3LYP/6-31G**). Bond lengths are given in Å and angles in degrees. Fo...

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Figure 9: Calculated structure of 7b-a (B3LYP/6-31G**). For other conformers (7b-b and 7b-c) and full details...

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Published 02 Jan 2015

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4-Pyridylnitrene and 2-pyrazinylcarbene

Curt Wentrup,
Ales Reisinger and
David Kvaskoff

Beilstein J. Org. Chem. 2013, 9, 754–760, doi:10.3762/bjoc.9.85

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Scheme 1: Phenylnitrene–2-pyridylcarbene rearrangement.

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Scheme 2: Type I and type II ring opening and ring expansion in 3- and 2-pyridylnitrenes, respectively.

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Scheme 3: FVT reactions of 4-azidopyridine (18), 2-(5-tetrazolyl)pyrazine (23) and triazolo[1,5-a]pyrazine (24...

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Figure 1: Difference-IR spectrum of 2-diazomethylpyrazine (22) (positive peaks) in Ar matrix at 7 K, obtained...

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Figure 2: Ar matrix IR-difference spectra showing the products of broadband UV photolysis of 4-azidopyridine (...

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Figure 3: Top: calculated IR spectrum of 20 at the B3LYP/6-31G* level (wavenumbers scaled by 0.9613): ν’ (rel...

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Figure 4: Bottom: IR spectrum from the matrix photolysis of azide 18 after the azide has been depleted comple...

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Scheme 4: Photolysis reactions of azide 18 and triazole 24 in Ar matrix.

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Published 17 Apr 2013

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3-Pyridylnitrene, 2- and 4-pyrimidinylcarbenes, 3-quinolylnitrenes, and 4-quinazolinylcarbenes. Interconversion, ring expansion to diazacycloheptatetraenes, ring opening to nitrile ylides, and ring contraction to cyanopyrroles and cyanoindoles

Curt Wentrup,
Nguyen Mong Lan,
Adelheid Lukosch,
Pawel Bednarek and
David Kvaskoff

Beilstein J. Org. Chem. 2013, 9, 743–753, doi:10.3762/bjoc.9.84

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Scheme 1: 4-Pyridylnitrene–2-pyrazinylcarbene interconversion.

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Scheme 2: Ring expansion and ring contraction in 2-pyridylnitrene (4).

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Scheme 3: Ring opening and ring expansion in 3-pyridylnitrene (10).

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Scheme 4: Ring opening and ring contraction in 3-pyridylnitrene (10) and diazacycloheptatetraene 16.

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Figure 1: Energy profile for the ring opening and ring contraction in 3-pyridylnitrene 10 and 1,6-diazacycloh...

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Scheme 5: Potential direct ring contraction in 3-pyridylnitrene (10).

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Scheme 6: Ring contraction by ring opening to nitrile ylide 11.

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Scheme 7: Generation of pyrimidinyldiazomethanes and pyrimidinylcarbenes.

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Scheme 8: Formation of cyanopyrroles by FVT of tetrazolylpyrimidines.

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Scheme 9: Rearrangements of pyrimidinylcarbenes to cyanopyrroles via nitrile ylides 31 and 37.

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Scheme 10: Rearrangements of phenyl(dimethylpyrimidinyl)carbene.

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Scheme 11: Photolysis of 3-azido-2-phenylquinoline.

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Figure 2: IR difference spectra from the photolysis of 3-azido-2-phenylquinoline (44) in Ar matrix. (a) Calcu...

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Figure 3: UV–vis spectra from the sequential photolysis of 3-azido-2-phenylquinoline (44) in Ar matrix at 310...

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Scheme 12: Preparative FVT of 3-azido-2-phenylquinoline.

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Scheme 13: FVT of 2-phenyl-4-quinazolinylcarbene precursors.

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Published 17 Apr 2013

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Synthesis of functionalized macrocyclic derivatives of trioxabicyclo[3.3.0]nonadiene

Sabine Leber,
Gert Kollenz and
Curt Wentrup

Beilstein J. Org. Chem. 2012, 8, 738–743, doi:10.3762/bjoc.8.83

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Scheme 1: Synthesis of macrocyclic bisdioxine derivatives (R,S-form of 4 and S-form of 5 shown; see Supporting Information File 1 for deta...

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Scheme 2: Synthesis of the 1,2,4-trisubstituted aryl derivatives.

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Scheme 3: Synthesis of the 1,2,3-trisubstituted aryl derivatives.

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Scheme 4: Synthesis of the tetraoxaadamantane derivative 14.

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Published 15 May 2012

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