TY - JOUR
T1 - Asymmetric photosensitized addition of methanol to (R)-(+)-(Z)-limonene in a microreactor
AU - Sakeda, Kosaku
AU - Wakabayashi, Kazuhito
AU - Matsushita, Yoshihisa
AU - Ichimura, Teijiro
AU - Suzuki, Tadashi
AU - Wada, Takehiko
AU - Inoue, Yoshihisa
N1 - Funding Information:
The authors thank Prof. Y. Fujimoto and Dr. N. Hara (Tokyo Tech) for valuable advice and experimental support for photoproduct isolation. This work was supported by a Grant-in-Aid for Scientific Research (no. 16310095) from the Ministry of Education, Culture, Sports and Technology of Japan, and the New Energy and Industrial Technology Development Organization (NEDO), Project of Development of Microspace and Nanospace Reaction Environment Technology for Functional Materials.
PY - 2007/12/15
Y1 - 2007/12/15
N2 - 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.
AB - 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.
KW - (R)-(+)-(Z)-Limonene
KW - Asymmetric reaction
KW - Diastereomeric excess
KW - Microreactor
KW - Photosensitized reaction
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U2 - 10.1016/j.jphotochem.2007.05.019
DO - 10.1016/j.jphotochem.2007.05.019
M3 - Article
AN - SCOPUS:35349024816
SN - 1010-6030
VL - 192
SP - 166
EP - 171
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
IS - 2-3
ER -