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A Simple Method for the Replacement of the OH Group in Free Carboxylic Acids by the Phosphonium Ylide Group
Author(s) -
Bestmann Hans Jürgen,
Dostalek Roman,
Bauroth Bernd
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199210641
Subject(s) - ylide , chemistry , hexamethyldisiloxane , phosphonium , trimethylsilyl , yield (engineering) , tartaric acid , group (periodic table) , organic chemistry , materials science , physics , plasma , quantum mechanics , metallurgy , citric acid
Acyl ylides and hexamethyldisiloxane are produced in the one‐pot reaction of free carboxylic acids with bis(trimethylsilyl)methylenetriphenylphosphorane [Eq. (a)]. Dicarboxylic acids and amino acids also undergo this reaction; only O ‐protected tartaric acids and monomethyl tartrates yield undefined elimination products.