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Synthesis and crystallographic analysis ofmeso-2,3-difluoro-1,4-butanediol andmeso-1,4-dibenzyloxy-2,3-difluorobutane

Synthesis and crystallographic analysis ofmeso-2,3-difluoro-1,4-butanediol andmeso-1,4-dibenzyloxy-2,3-difluorobutane
Synthesis and crystallographic analysis ofmeso-2,3-difluoro-1,4-butanediol andmeso-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 attempts to achieve chain extension through addition of alkyl Grignard and acetylide nucleophiles failed.
building block, epoxide opening, gauche effect, organofluorine, vicinal difluoride
1860-5397
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Leung, Leo
bc749c61-15c6-4c7c-9396-db2c93ac3fd9
Nonnenmacher, Jean
71e640e7-793b-445d-9a49-7c9999aff111
Tizzard, Graham
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Leung, Leo
bc749c61-15c6-4c7c-9396-db2c93ac3fd9
Nonnenmacher, Jean
71e640e7-793b-445d-9a49-7c9999aff111
Tizzard, Graham
8474c0fa-40df-43a6-a662-7f3c4722dbf2

Linclau, Bruno, Leung, Leo, Nonnenmacher, Jean and Tizzard, Graham (2010) Synthesis and crystallographic analysis ofmeso-2,3-difluoro-1,4-butanediol andmeso-1,4-dibenzyloxy-2,3-difluorobutane. Beilstein Journal of Organic Chemistry, 6. (doi:10.3762/bjoc.6.62). (PMID:20625521)

Record type: Article

Abstract

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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Published date: June 2010
Keywords: building block, epoxide opening, gauche effect, organofluorine, vicinal difluoride
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Identifiers

Local EPrints ID: 170451
URI: http://eprints.soton.ac.uk/id/eprint/170451
DOI: doi:10.3762/bjoc.6.62
ISSN: 1860-5397
PURE UUID: accd0fef-c559-4ffd-8fbc-abce2342200e
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170
ORCID for Graham Tizzard: ORCID iD orcid.org/0000-0002-1577-5779

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Date deposited: 06 Jan 2011 15:36
Last modified: 14 Mar 2024 02:46

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Author: Bruno Linclau ORCID iD
Author: Leo Leung
Author: Jean Nonnenmacher
Author: Graham Tizzard ORCID iD

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