Chin. J. Org. Chem. ›› 1990, Vol. 10 ›› Issue (5): 427-431. Previous Articles     Next Articles

Original Articles

己二烯基烯丙基醚的Wittigσ迁移重排反应

李正名;王天生;高振衡   

  1. 南开大学元素有机化学研究所
  • 发布日期:1990-10-25

The wittig sigmatropic rearrangement of hexadienyl allyl enther

LI ZHENGMING;WANG TIANSHENG;GAO ZHENHENG   

  • Published:1990-10-25

(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

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