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

• with 3-bromopropanol followed by nitration of the resulting diol 6 (Scheme 2). The isomeric 1,2,3-trisubstituted aromatic 10 was obtained by etherification of nitroresorcinol (Scheme 3). The two diols 7 and 10 reacted readily with the diacid dichloride 3 in boiling toluene in the presence of

Carbasugar analogues of galactofuranosides: α-O-linked derivatives

• Jens Frigell and
• Ian Cumpstey

Beilstein J. Org. Chem. 2010, 6, 1127–1131, doi:10.3762/bjoc.6.129

• exemplify the method. Keywords: carbasugars; etherification; galactofuranose; glycomimetics; pseudodisaccharides; regioselective; Introduction Galactofuranose is found in nature as a component of glycoconjugates in many microorganisms [1][2]. Galactofuranosides with the α configuration are rather less

Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive

• Joachim E. Klee and
• Uwe Lehmann

Beilstein J. Org. Chem. 2010, 6, 766–772, doi:10.3762/bjoc.6.95

• acrylate and formaldehyde, and subsequent etherification of the obtained product with diols and phosphorylation using POCl3. The polymerization enthalpy of 2-(ω-phosphonooxy-2-oxaalkyl)acrylates 3 as measured by DSC ranges from −29 to −53 kJ·mol−1. The shear bond strength of adhesive compositions 4

• , comprising of phosphoric acid ester moieties, were synthesized via a three step synthesis via Baylis–Hillman reaction of ethyl acrylate and formaldehyde, and subsequent etherification of the obtained product with diols and phosphorylation using POCl3 (Scheme 1, Table 1). The double bonds in 3 are evident in

• -phosphonooxy-2-oxaalkyl)acrylate monomers 3 with phosphoric acid moieties and alkyl as well as oxyalkyl spacers were synthesized in three steps via Baylis–Hillman reaction of ethyl acrylate and formaldehyde, and subsequent etherification of the obtained product with diols and phosphorylation using POCl3. The

Synthesis of bis(3-{[2-(allyloxy)ethoxy]methyl}-2,4,6-trimethylbenzoyl)(phenyl)phosphine oxide – a tailor-made photoinitiator for dental adhesives

• Norbert Moszner,
• Iris Lamparth,
• Jörg Angermann,
• Urs Karl Fischer,
• Frank Zeuner,
• Thorsten Bock,
• Robert Liska and
• Volker Rheinberger

Beilstein J. Org. Chem. 2010, 6, No. 26, doi:10.3762/bjoc.6.26

• ) was synthesized starting from 3-(chloromethyl)-2,4,6-trimethylbenzoic acid by the dichlorophosphine route. The substituent was introduced by etherification with 2-(allyloxy)ethanol. In the second step, 3-{[2-(allyloxy)ethoxy]methyl}-2,4,6-trimethylbenzoic acid was chlorinated. The formed acid chloride

• in acetonitrile (10−3 mol/L). DSC-plot of a mixture of Bis-GMA (42 wt %), UDMA (37 wt %), TEGDMA (21 wt %) and the PI WBAPO or BAPO. Bisacylphosphine oxide with improved solubility in polar solvents. Etherification of 3-(chloromethyl)-2,4,6-trimethylbenzoic acid and chlorination of 1. Rearrangement

Low temperature enantiotropic nematic phases from V-shaped, shape-persistent molecules

• Matthias Lehmann and
• Jens Seltmann

Beilstein J. Org. Chem. 2009, 5, No. 73, doi:10.3762/bjoc.5.73

• nematogens were prepared following the recent optimised procedure [25], using the mono-protected diethynylbenzene derivative 4 as a key compound (Scheme 1). The peripheral aromatic units 5 were obtained by etherification of 4-iodophenol with the corresponding ethyl ω-bromoalkanoate [28]. Cross-coupling of

Ring strain and total syntheses of modified macrocycles of the isoplagiochin type

• Andreas Speicher,
• Timo Backes,
• Kerstin Hesidens and
• Jürgen Kolz

Beilstein J. Org. Chem. 2009, 5, No. 71, doi:10.3762/bjoc.5.71

• simple modification, e. g. etherification. However, the flexibility and stability of the molecule is only slightly modified by introducing an unsaturated two-carbon bridge between rings b and c. Structures of isoplagiochins C (1) and D (2) (with aryl fragments a–d and possible conformational barriers A–D

Influence of spacer chain lengths and polar terminal groups on the mesomorphic properties of tethered 5-phenylpyrimidines

• Gundula F. Starkulla,
• Elisabeth Kapatsina,
• Angelika Baro,
• Frank Giesselmann,
• Stefan Tussetschläger,
• Martin Kaller and
• Sabine Laschat

Beilstein J. Org. Chem. 2009, 5, No. 63, doi:10.3762/bjoc.5.63

• 55, 70569 Stuttgart, Germany 10.3762/bjoc.5.63 Abstract Based on 5-(4-hydroxyphenyl)-2-octylpyrimidine 8, 5-phenylpyrimidine derivatives 3–7, 9 with different spacer chain lengths (C2 up to C6) and different terminal polar groups (Br, Cl, N3, OH, CN) were synthesized by etherification and

• 23 up to 60% yield. When 1,3-dibromopropane was used, 27% of the elimination product 9 was isolated as byproduct. For comparison the corresponding 4-allyloxy-4′-octylbiphenyl 11 was prepared in 49% yield by allylation of 4-hydroxy-4′-octylbiphenyl. Compound 3a was obtained by etherification of 5-(4

Synthesis of methylenebisamides using CC- or DCMT- activated DMSO

• Qiang Wang,
• Lili Sun,
• Yu Jiang and
• Chunbao Li

Beilstein J. Org. Chem. 2008, 4, No. 51, doi:10.3762/bjoc.4.51

• on the chlorination [10] and etherification [11] of benzyl alcohols and from other references [12][13][14], we believe the reaction between 2,4,6-trichloro[1,3,5]triazine (cyanogen chloride, or CC) and DMSO produces a reactive sulfonium salt intermediate. Therefore, it was of interest to study the

Recent progress on the total synthesis of acetogenins from Annonaceae

• Nianguang Li,
• Zhihao Shi,
• Yuping Tang,
• Jianwei Chen and
• Xiang Li

Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48

• materials (e.g. amino acids, sugars, tartaric acid, etc.) or on asymmetric reactions {e.g. Sharpless asymmetric epoxidation (AE), Sharpless asymmetric dihydroxylation (AD), diastereoselective Williamson etherification, etc.}. Semi-synthesis of natural ACGs as well as derivatised ACGs (e.g. amines, esters

• enantioselectively controlled manner (Scheme 30) [85]. The appropriate bis-THF ring system 227 was constructed using a Williamson type etherification reaction on a functionalized bis-mesylate intermediate. A Sonogashira cross-coupling reaction of the terminal acetylene 228 with vinyl iodide 229 followed by