Synthesis and Diels-Alder reactions of 1,2-dimethylene[2.n]metacyclophanes

Takehiko Yamato; Shinpei Miyamoto; Tohru Hironaka; Yoshinori Miura

doi:10.1021/ol0483403

Synthesis and Diels-Alder reactions of 1,2-dimethylene[2.n]metacyclophanes

Org Lett. 2005 Jan 6;7(1):3-6. doi: 10.1021/ol0483403.

Authors

Takehiko Yamato¹, Shinpei Miyamoto, Tohru Hironaka, Yoshinori Miura

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga 840-8502, Japan. yamatot@cc.saga-u.ac.jp

PMID: 15624963
DOI: 10.1021/ol0483403

Abstract

The Diels-Alder reaction of 1,2-dimethylene[2.n]MCPs (MCP = metacyclophane) with suitable dienophiles followed by aromatization and photoinduced or FeCl(3)-induced transannular cyclization afforded phenanthrene-anellated polycyclic aromatic hydrocarbons, which were found to adopt helical chirality in the solid state.