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

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

Research output: Contribution to journalArticle

11 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 Na Y 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 meso cis-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
StatePublished - Jan 1 2005
Externally publishedYes

Fingerprint

Photoisomerization
Carboxylic Acids
carboxylic acids
Zeolites
Derivatives
Isomers
isomers
excitation
Photochemistry
Photochemical reactions
Isomerization
Excited states
zeolites
photochemical reactions
isomerization
cleavage
induction
diphenylcyclopropane

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Cell Biology
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biophysics

Cite this

Mechanism of photoisomerization of optically pure trans-2,3-diphenylcyclopropane-1-carboxylic acid derivatives. / Sivaguru, J.; Wada, Takehiko; Origane, Yumi; Inoue, Yoshihisa; Ramamurthy, Vaidhyanathan.

In: Photochemical and Photobiological Sciences, Vol. 4, No. 1, 01.01.2005, p. 119-127.

Research output: Contribution to journalArticle

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