Asymmetric photosensitized addition of methanol to (R)-(+)-(Z)-limonene in a microreactor

Kosaku Sakeda, Kazuhito Wakabayashi, Yoshihisa Matsushita, Teijiro Ichimura, Tadashi Suzuki, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

Photosensitized diastereodifferentiating addition of methanol to (R)-(+)-(Z)-limonene in a microreactor was investigated. The quantity of photoproducts, cis- and trans-4-isopropenyl-1-methoxy-1-methylcyclohexane, increases with increasing period of irradiation by a mercury lamp, and the diastereomeric excess (de) of the photoadduct is slightly larger than that obtained in a batch reaction system. The reaction rate constants for the production of the cis and trans isomers were successfully obtained by using the steady state approximation. The larger de value in the microreactor was found to result from the suppression of the sequential side reaction processes. The feasibility of microreaction system for the photoreaction will be discussed.

Original languageEnglish
Pages (from-to)166-171
Number of pages6
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume192
Issue number2-3
DOIs
Publication statusPublished - 2007 Dec 15
Externally publishedYes

Keywords

  • (R)-(+)-(Z)-Limonene
  • Asymmetric reaction
  • Diastereomeric excess
  • Microreactor
  • Photosensitized reaction

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Physics and Astronomy(all)

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