Mechanism of photoisomerization of optically pure trans-2,3-diphenylcyclopropane-1-carboxylic acid derivatives

J. Sivaguru, Takehiko Wada, Yumi Origane, Yoshihisa Inoue, V. Ramamurthy

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

The photochemistry of optically pure isomers of α-methylbenzylamide of trans-2,3-diphenylcyclopropane-1-carboxylic acid has been examined in isotropic solution and within zeolites. The results suggest that these isomerize through cleavage of C2–C3 bond. The direct excitation in solution leads to non-equilibrating 1,3-singlet diradical intermediates whereas triplet sensitization results in equilibrating 1,3-triplet diradical intermediates. The direct excitation within NaY zeolite seems to result in equilibrating zwitterionic intermediates. Studies on the optically pure trans isomers allow one to understand the mechanism of chiral induction during the photoisomerization of mesocis-2,3-diphenylcyclopropane-1-carboxylic acid. The current study has clarified the nature of the excited states involved during the classic (R)-N-acetyl-1-naphthylethylamine sensitized isomerization of 1,2-diphenylcyclopropane.

Original languageEnglish
Pages (from-to)119-127
Number of pages9
JournalPhotochemical and Photobiological Sciences
Volume4
Issue number1
DOIs
Publication statusPublished - 2005 Dec 22
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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