Photodimerization of benzenes in strained dihetera[3.3]metacyclophanes

  • Higuchi H
  • Kobayashi E
  • Sakata Y
 et al. 
  • 7

    Readers

    Mendeley users who have this article in their library.
  • 25

    Citations

    Citations of this article.

Abstract

Double- to quadruple-layered dihetera[3.3]metacyclophanes containing O, S, and Se atoms in the bridge chains were synthesized by the usual methods. On irradiation, three quadruple-layered cyclophanes 1a-c undergo a photodimerization of two inner benzenes to give good yields of novel cage compounds 2a-c which revert thermally to the starting cyclophanes. The driving forces for such intriguing photoreactions were studied with respect to the strain of the benzene, effect of chalcogen atom species, interfacial constraint, etc., using several reference cyclophanes. It is concluded that the face-to-face stacking of two fairly strained benzene nuclei is responsible for the photodimerization and the two outer benzenes are required for the effective interconversion between quadruple-layered diheteracyclophanes and their isomeric cage compounds. © 1986.

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document

Authors

  • Hiroyuki Higuchi

  • Eiji Kobayashi

  • Yoshiteru Sakata

  • Soichi Misumi

Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free