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Paper | Special issue | Vol 79, No. 1, 2009, pp.865-872
Published online, 10th December, 2008
DOI: 10.3987/COM-08-S(D)57
Effect of Aryl Substituents on Intramolecular Cyclization of 2,2’-Biphenoquinones

Naoto Hayashi,* Akifumi Kanda, Taku Kamoto, Hiroyuki Higuchi, and Takeyuki Akita*

*Department of Chemistry, Faculty of Science, Toyama University, Gofuku 3190, Toyama 930, Japan

Abstract

Effect of aryl substituents on intramolecular cyclizations of 3,3',5,5'-tetraaryl-2,2'-biphenoquinones (Ar = phenyl (1a) and 4-methoxyphenyl (1b)) has been studied. In benzene, 1a gave 2,4,6,8-tetraphenyldibenzofuran-1-ol (10) gradually as a main product, indicating the phenyl substituents preferred to stabilize the intermediate by delocalization of the negative charge rather than that of the positive one. In contrast, the reaction of 1b occurred spontaneously in order to give a complex mixture, which should be due to 4-methoxyphenyl substituent at the 3 position.