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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 4, Number 1
BKCSDE 4(1)
January 20, 1983

Title	MO Theoretical Studies on Stereoelectronic Control in the Addition Reaction of 1, 4-Benzoquinone-4-(O-methyloxime)
Author	Ikchoon Lee, Eun Sook Han
Keywords
Abstract	The chlorine addition and Diels-Alder cycloaddition of cyclopentadiene to 1, 4-benzoquinone-4-(O-methyloxime) have been studied MO theoretically. It has been shown that the reactions occur predominantly to the quinone ring double bond which is oriented anti to the nitrogen lone pair due to an n-σ* interaction between the nitrogen lone pair, n, and the app. vicinal bond, causing the π bond to be weakened and destabilized due to the less conjugation from reduced delocalization.
Page	41 - 44
Full Text	PDF

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