The wittig sigmatropic rearrangement of hexadienyl allyl enther

Abstract

(E,E)-2,4-Hexadienyl allyl ether underwent Wittig [2.3]-sigmatropic rearrangement reaction in THF to give a mixture of (E,E)-1,5,7-nonatrien-4-ol (I) and (E)-4-vinyl-1,5-heptadien-3-ol. If the reaction proceeded in mixed solvent of THF-HMPA, a single product I resulted. The rearrangement of (Z,E)-2,4-hexadienyl allyl ether in THF-HMPA gave (Z,E)-1,5,7-nonatrien-4-ol, as well as the (E,E)-isomer I. The mechanisms were discussed.

Key words: INFRARED SPECTROPHOTOMETRY, REACTION MECHANISM, MASS SPECTROGRAPHY, WITTIG REACTION, ALLYL GROUP, ETHER, C13 NMR SPECTROMETRY, HEXADIENE P, REARRANGEMENT REACTION, PROTON MAGNETIC RESONANCE SPECTROMETRY

CLC Number:

O621

Cite this article

LI ZHENGMING;WANG TIANSHENG;GAO ZHENHENG. The wittig sigmatropic rearrangement of hexadienyl allyl enther[J]. Chin. J. Org. Chem., 1990, 10(5): 427-431.

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己二烯基烯丙基醚的Wittigσ迁移重排反应