Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 49, Pages 16500-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja8076999
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beta-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].
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