Canadian Journal of Chemistry

The importance of conformation in the reactivity of radical cations. Changing configuration at saturated carbon centres

AL Perrott, DR Arnold

Index: Perrott, Allyson L.; Arnold, Donald R. Canadian Journal of Chemistry, 1992 ,  vol. 70,  # 1  p. 272 - 279

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Citation Number: 35

Abstract

Irradiation of an acetonitrile solution of cis 1-methyl-2-phenylcyclopentane (1 b cis); 1, 4- dicyanobenzene (2), an electron-accepting photosensitizer; and 2, 4, 6-collidine (3), a nonnucleophilic base, leads to configurational isomerization of the cyclopentane; the photostationary state lies> 99% in favour of the trans isomer. The mechanism proposed for this reaction involves formation of the radical cation of 1 b cis by photoinduced electron ...