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Fritsch−Buttenberg−Wiechell Rearrangement in the Aliphatic Series

2000; American Chemical Society; Volume: 2; Issue: 4 Linguagem: Inglês

10.1021/ol991117z

1523-7060

H. Rezaei, Shigeo Yamanoi, Fabrice Chemla, J. F. NORMANT,

Cyclopropane Reaction Mechanisms

Substituted vinylidene zinc carbenoids undergo a Fritsch−Buttenberg−Wiechell rearrangement. The migratory aptitude of the two groups R/R1 was studied by 13C labeling experiments and depends on the degree of substitution in R and R1 groups and on the presence of an oxygen atom in the allylic position.