Author:
Abell AD,Massy-Westropp RA
Abstract
It
has been established that the Wittig reaction between
cyclic anhydrides and methoxycarbonylmethylenetriphenylphosphorane,
a reaction used for the preparation of enol-lactones,
proceeds via an acyclic intermediate acylated
phosphorane for the three classes of anhydrides studied: succinic,
maleic and phthalic. The
formation of the acyclic intermediate can be irreversible or reversible, depending
on the structure of the anhydride. The stereochemistry of the enol-lactones produced is not controlled by the initial
reaction of the anhydride with the ylide but either
during or after cyclization of the acyclic intermediate. Product formation
appears to be under kinetic control with all the anhydrides studied. The
influence of substituents in substituted phthalic anhydrides
has been investigated.
Cited by
31 articles.
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