(2,2′)(2,2′)Biphenylophanetriyne: A Twisted Biphenylophane with a Highly Distorted Diacetylene Bridge

Shunpei Nobusue, Hiroshi Yamane, Hirokazu Miyoshi, Tobe Yoshito*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

Biphenylophane 1 bridged by acetylene and diacetylene linkages was synthesized. X-ray analysis revealed its highly deformed diacetylene unit with a bond angle of 160°. Enantiomers of 1 resolved by chiral HPLC underwent facile racemization with an activation energy of 90.6 kJ mol-1. Transannular cyclization of 1 was induced by heating to generate benzyne intermediate 8, which was intercepted by furan to give 9, and by treatment with bromine to give dibromodibenzopicene (10).

Original languageEnglish
Pages (from-to)1940-1943
Number of pages4
JournalOrganic Letters
Volume16
Issue number7
DOIs
StatePublished - 4 Apr 2014

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