The kinetically-controlled Cope rearrangement of 2,5-bis(4-methoxyphenyl)hexa-1,5-dienes induced by photosensitised electron transfer

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Hiroshi Ikeda, Akito Ishida, Toshihiko Takasaki, Sachiko Tojo, Setsuo Takamuku and Tsutomu Miyashi


Abstract

The photoinduced electron-transfer Cope rearrangement of (E,E)-3,6-bis(4-methoxyphenyl)octa-2,6-diene (E,E)-1 is kinetically controlled and affords quantitatively the thermodynamically less stable (±)-3,4-dimethyl-2,5-bis(4-methoxyphenyl)hexa-1,5-diene (±)-1 at -80 °C in sharp contrast to the thermodynamically-controlled thermal Cope rearrangement.


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