The University of Southampton
University of Southampton Institutional Repository

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.

Full text not available from this repository.

More information

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

Identifiers

Local EPrints ID: 170451
URI: http://eprints.soton.ac.uk/id/eprint/170451
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

Catalogue record

Date deposited: 06 Jan 2011 15:36
Last modified: 07 Oct 2020 07:54

Export record

Altmetrics

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×