Biphenyltetrols and Dibenzofuranones from Oxidative Coupling of Resorcinols with 4??Alkylpyrocatechols: New Ciues to the Mechanism of Insect Cuticle Sclerotization

M Miessner, O Crescenzi, A Napolitano…

Index: Miessner, Merle; Crescenzi, Orlando; Napolitano, Alessandra; Prota, Giuseppe; Andersen, Svend Olav; Peter, Martin G. Helvetica Chimica Acta, 1991 , vol. 74, # 6 p. 1205 - 1212

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Citation Number: 11

Abstract

Abstract Oxidation of 4-alkylpyrocatechols 2 by means of an insect diphenoloxidase (laccase) or K 3 [Fe (CN) 6] yields, in the presence of resorcinols 1 (R 2 [DOUBLE BOND] H), complex mixtures of products from which biphenyltetrols 3 (R 3 [DOUBLE BOND] H) and dibenzofuranones 5 and 6 were isolated. It is suggested that similar homo-coupling products are formed from pyrocatechols 2b and 2c in insects during cuticle sclerotization.