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Convergent and stereoselective synthesis of trisubstituted E-alkenyl bromides and iodides via beta-oxido phosphonium ylides.

Abstract:
β-Oxido phosphonium ylides, generated in situ from aldehydes and Wittig reagents [alkylidene(triphenyl)phosphoranes, other than ethylidene(triphenyl)phosphorane], react readily with electrophilic halogen sources to form predominantly or exclusively E-bromo- or iodosubstituted alkenes. The stereochemical outcome on halogenation is remarkably sensitive to alkylidene size [ethylidene(triphenyl)phosphorane is highly Z-selective]. Copyright © 2008 American Chemical Society.
Publication status:
Published

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Publisher copy:
10.1021/ja8076999

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Journal of the American Chemical Society
Volume:
130
Issue:
49
Pages:
16500-16501
Publication date:
2008-12-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:c2ab800d-c0ad-4c68-9685-c366b14a8508
Source identifiers:
34500
Local pid:
pubs:34500
Language:
English

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