Acetoxycarbenes: modified oxacarbenes with enhanced reactivity

RA Moss, S Xue, W Liu

Index: Moss, Robert A.; Xue, Song; Liu, Weiguo Journal of the American Chemical Society, 1994 , vol. 116, # 4 p. 1583 - 1584

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Citation Number: 24

Abstract

The strongly resonance donating methoxy group stabilizes singlet relative to triplet carbenes,'mitigates their reactivity,” and accentuates their nucleophilic~ r 0 perties. s~ Modulation or “tuning” of the electronic properties of the oxa substituent should lead to “designer” oxacarbenes of varied reactivity and synthetic utility. For example, the trifluoroethoxy group, CF3CH20, is a weaker resonancedonor (u~+-0.56) 8-~ 0than ...