Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane

A large-scale synthesis of meso-2,3-difluoro-1,4-butanediol in 5 steps from (Z)-but-2-enediol is described. Crystallographic analysis of the diol and the corresponding benzyl ether reveals an anti conformation of the vicinal difluoride moiety. Monosilylation of the diol is high-yielding but all atte...

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Detalles Bibliográficos
Autores principales: Linclau, Bruno, Leung, Leo, Nonnenmacher, Jean, Tizzard, Graham
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2010
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2900908/
https://www.ncbi.nlm.nih.gov/pubmed/20625521
http://dx.doi.org/10.3762/bjoc.6.62
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author Linclau, Bruno
Leung, Leo
Nonnenmacher, Jean
Tizzard, Graham
author_facet Linclau, Bruno
Leung, Leo
Nonnenmacher, Jean
Tizzard, Graham
author_sort Linclau, Bruno
collection PubMed
description A large-scale synthesis of meso-2,3-difluoro-1,4-butanediol in 5 steps from (Z)-but-2-enediol is described. Crystallographic analysis of the diol and the corresponding benzyl ether reveals an anti conformation of the vicinal difluoride moiety. Monosilylation of the diol is high-yielding but all attempts to achieve chain extension through addition of alkyl Grignard and acetylide nucleophiles failed.
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spelling pubmed-29009082010-07-12 Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane Linclau, Bruno Leung, Leo Nonnenmacher, Jean Tizzard, Graham Beilstein J Org Chem Full Research Paper A large-scale synthesis of meso-2,3-difluoro-1,4-butanediol in 5 steps from (Z)-but-2-enediol is described. Crystallographic analysis of the diol and the corresponding benzyl ether reveals an anti conformation of the vicinal difluoride moiety. Monosilylation of the diol is high-yielding but all attempts to achieve chain extension through addition of alkyl Grignard and acetylide nucleophiles failed. Beilstein-Institut 2010-06-08 /pmc/articles/PMC2900908/ /pubmed/20625521 http://dx.doi.org/10.3762/bjoc.6.62 Text en Copyright © 2010, Linclau et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Linclau, Bruno
Leung, Leo
Nonnenmacher, Jean
Tizzard, Graham
Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane
title Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane
title_full Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane
title_fullStr Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane
title_full_unstemmed Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane
title_short Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane
title_sort synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2900908/
https://www.ncbi.nlm.nih.gov/pubmed/20625521
http://dx.doi.org/10.3762/bjoc.6.62
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