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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 20, Number 5
BKCSDE 20(5)
May 20, 1999 

 
Title
Photocyclization of α-(o-Ethylphenyl)acetophenone in Zeolites
Author
Taehee Noh, Kyungin Choi, Hyeoksoon Kwon, Dong Jo Chang, Bong Ser Park
Keywords
Abstract
The diastereoselectivity in the photocyclization of α-(o-ethylphenyl)acetophenone(1) to 1-methyl-2-phenyl-2-indanol was studied in zeolites X and Y, and compared with that in isotropic solvents. The yields of E-diastereomer at the irradiation of 1 in protic solvents were higher than those in aprotic solvents. The ratios of E-diastereomer to Z-diastereomer in zeolites X and Y were much higher than those in isotropic solvents. The E/Z ratios at the irradiation of 1 in zeolites X were also found to be dependent on the cations present. As the cation size increased from Li+ to Cs+, the ratio decreased. However, any pattern in the E/Z ratios was not found in zeolites Y. The diastereoselectivity observed in the zeolites was interpreted by the conformational restriction imposed by the cavity size. An efficient oxidation of 1 in zeolites RbX and CsX was also observed.
Page
539 - 542
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