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Synthesis of Alkenyl‐Substituted Allenecarboxylates
Author(s) -
Lang Robert Werner,
KohlMines Elisabeth,
Hansen HansJürgen
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680820
Subject(s) - chemistry , wittig reaction , phosphorane , moiety , phosphonium salt , phosphonium , stereochemistry , ylide , organic chemistry , medicinal chemistry , salt (chemistry)
The Wittig olefination of decanoyl chloride by using the phosphonium salt 1 in the presence of two equivalents of Et 3 N represents a one‐step synthesis of the racemic form of the naturally occurring pheromone (–)‐ 2 which contains an alkenyl‐substituted allenic moiety (ef. Scheme 1) . It is also shown, that unsaturated acyl chlorides which contain at least one γ‐H‐atom undergo the Wittig reaction with an appropriate phosphorane yielding γ‐alkenyl‐substituted α‐allenic esters and α‐allenic γ‐lactones, respectively (ef. Schemes 2 and 3) .