Abstract

1-Alkenyl chlorides, bromides or iodides, e.g., cis-1-chloro-1-octene, can be obtained with very high cis selectivities by Wittig reactions with a-chloro, a-bromo and a-iodo ylides derived from (2-MeOCH2C6H4)3P. The corresponding a-methoxy substituted ylide produces enol ethers with remarkably high cis/trans ratios. Pd(II)-catalyzed coupling of (Z)-1-iodo-1-heptene with Et acrylate affords Et (2E,4Z)-2,4-decadienoate, the Bartlett pear fragrance, in almost quant. yield. [on SciFinder (R)]

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