Synthesis of hydroxyquinones and related compounds: semisquaric acids,(.+-.)-terreic acid,(.+-.)-perezone and (.+-.)-isoperezone

A Enhsen, K Karabelas, JM Heerding…

Index: Enhsen, Alfons; Karabelas, Kostas; Heerding, Julia M.; Moore, Harold W. Journal of Organic Chemistry, 1990 , vol. 55, # 4 p. 1177 - 1185

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Citation Number: 53

Abstract

tert-Butoxyquinones were prepared from the thermal ring expansion of 4-alkynyl-, 4-alkenyl-, and 4-aryl-tert-butoxycyclobutenones and shown to be readily converted to hydroxyquinones upon treatment with tri-fluoroacetic acid at low temperature. This is a useful transformation since no reliable general route to hydroxyquinones has previously been available. The synthetic scope of this methodology as well as its specific utilization in ...