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C ‐Phosphoniophosphaalkenes as Precursors of 1σ 4 ,3σ 2 ‐Diphosphaallenes: Scope and Limitations
Author(s) -
Martin David,
Gornitzka Heinz,
Baceiredo Antoine,
Bertrand Guy
Publication year - 2005
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200500014
Subject(s) - chemistry , electrophile , cycloaddition , lewis acids and bases , medicinal chemistry , base (topology) , organic chemistry , stereochemistry , catalysis , mathematical analysis , mathematics
The study of a general synthetic route to 1σ 4 ,3σ 2 ‐diphosphaallenes involving the reaction of LiHMDS with C ‐phosphoniophosphaalkenes is reported. The choice of the base is critical since the precursors are highly electrophilic species that react cleanly with methyl‐, butyl‐, mesityl‐, or tert‐ butyllithium to afford C ‐phosphanylphosphonium ylides. The role of the substituents at the σ 4 ‐phosphorus centre has alsobeen studied. The resulting phosphaallenes react cleanly with a Lewis acid and undergo [3+2] cycloaddition withazides to afford a five‐membered heterocycle in a three‐step process. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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