Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Reaction of 1,2-Dimethoxybiphenylene with Dichlorocarbene. Chemical Detection of the Bond Fixation in Biphenylene Derivatives
Masaru SatoKeiko InabaSeiji EbineJosuke Tsunetsugu
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1980 Volume 53 Issue 8 Pages 2334-2339

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Abstract

1,2-Dimethoxybiphenylene reacted with dichlorocarbene to give three chloro(methoxy)-6H-benzo[3,4]cyclobuta[1,2]cyclohepten-6-one derivatives, two chloro(methoxy)fluorenones and two dimethoxyfluorenones. The reaction with dibromocarbene gave similar products. The formation of these products serves as unequivocal chemical evidence for bond fixation of 1,2-dimethoxybiphenylene. The chloro(methoxy)-6H-benzo[3,4]cyclobuta-[1,2]cyclohepten-6-one was led to 9-chloro-5-hydroxy-6H-benzo[3,4]cyclobuta[1,2]cyclohepten-6-one, the first tropolone analogue of biphenylene. This compound was shown to exist in only one of the two possible tautomers in contrast with general monocyclic tropolones.

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