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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 12, Number 6
BKCSDE 12(6)
June 20, 1991

Title	Theoretical Studies on the Gas-Phase Wittig-Oxy-Cope Rearrangement of Deprotonated Diallyl Ether
Author	Chang Kon Kim, Ikchoon Lee*, Hai Whang Lee, Bon-Su Lee
Keywords
Abstract	The Wittig-oxy-Cope rearrangements of deprotonated diallyl ether, Ⅰ, CH2=CH-CH-O-CH2-CH=CH2, have been investigated theoretically by the AM1 method. A two step mechanism forming a Wittig product ion, Ⅱ, (CH2=CH) (CH2=CH-CH2) CHO-, through a radical-pair intermediate was found to provide the most favored reaction pathway in the Wittig rearrangement. The subsequent oxy-Cope rearrangement from species Ⅱ also involves a two step mechanism through a biradicaloid intermediate. The intramolecular proton transfer in Ⅰ (to form CH2=CH-CH2-O-CH-CH=CH2) is a higher activation energy barrier process compared to the Wittig and oxy-Cope rearrangements and is considered to be insignificant. These results are in good agreement with the condensed-phase as well as gas-phase experimental results.
Page	678 - 681
Full Text	PDF

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