Open AccessMechanism of Wittig reaction with cyclic anhydrides
Author(s) -
Margaret M. Kayser,
Krista L. Hatt,
Donald L. Hooper
Publication year - 1992
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v92-249
Subject(s) - chemistry , wittig reaction , adduct , enol , condensation , reaction mechanism , computational chemistry , trapping , organic chemistry , photochemistry , catalysis , ecology , biology , physics , thermodynamics
The reactions of stabilized phosphoranes with cyclic anhydrides give enol-lactones as final products. The initial condensation, however, leads to the formation of acyclic adducts that are observable by NMR, can be easily trapped, and, in some cases, can be isolated. A study of the mechanism of these condensations by NMR spectroscopic methods and by various trapping experiments is described and the reaction pathway is proposed.
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