Journal of Organic Chemistry p. 2530 - 2537 (1987)
Update date:2022-08-04
Topics:
Moore, Harold W.
Chow, Ken
Nguyen, Nghi V.
4-Alkynyl-3-azido-6-chloro-5-ethoxy-1,2-benzoquinones are shown to undergo thermolysis to (2-alkynyl-2-cyanoethenyl)ketenes.These conjugated ketenes undergo intramolecular cyclization to zwitterionic intermediates that proceed to highly substituted 4-cyanophenols via inter- or intramolecular trapping by nucleophilic attack at the aryl cation site.The mechanism and scope of these unusual transformations are discussed.
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