Cyclopropenes for the Stepwise Synthesis of 1,2,4,5-Tetraarylbenzenes via 1,4-Cyclohexadienes

This paper describes a synthetic approach to the synthesis of 1,2,4,5-tetraarylbenzene derivatives from cyclopropenes. The Lewis acid-mediated dimerization of cyclopropenes gives tricyclo­[3.1.0.02,4]­hexane derivatives. The subsequent thermal ring-opening reaction under solvent-free conditions give...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-11, Vol.87 (21), p.14833-14839
Main Authors: Kishida, Satoshi, Takano, Misaki, Sekiya, Takuya, Ukaji, Yutaka, Endo, Kohei
Format: Article
Language:English
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Summary:This paper describes a synthetic approach to the synthesis of 1,2,4,5-tetraarylbenzene derivatives from cyclopropenes. The Lewis acid-mediated dimerization of cyclopropenes gives tricyclo­[3.1.0.02,4]­hexane derivatives. The subsequent thermal ring-opening reaction under solvent-free conditions gives 1,4-cyclohexadienes bearing quaternary carbons. The novel Br2-mediated oxidative rearrangement of 1,4-cyclohexadienes takes place to give 1,2,4,5-tetraarylbenzene derivatives in high to excellent yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01261