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Journal article

Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine.

Abstract:
Terminal epoxides undergo lithium 2,2,6,6-tetramethylpiperidide-induced α-lithiation and subsequent interception with Ph(3)P to provide a new and direct entry to β-lithiooxyphosphonium ylides. The intermediacy of such an ylide is demonstrated by representative alkene-forming reactions with chloromethyl pivalate, benzaldehyde and CD(3)OD, giving a Z-allylic pivalate, a conjugated E-allylic alcohol and a partially deuterated terminal alkene, respectively, in modest yields.
Publication status:
Published

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Publisher copy:
10.3762/bjoc.8.219

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Beilstein journal of organic chemistry
Volume:
8
Pages:
1896-1900
Publication date:
2012-01-01
DOI:
EISSN:
1860-5397
ISSN:
1860-5397
Source identifiers:
365479
Language:
English
Keywords:
Pubs id:
pubs:365479
UUID:
uuid:6e248072-6d94-40bd-a0c6-8ae7a2f4953c
Local pid:
pubs:365479
Deposit date:
2013-11-16

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