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Photochemistry of some deoxybenzoins in micellar solutions. Cage effects, isotope effects, and magnetic field effects

Journal Article · · J. Am. Chem. Soc.; (United States)
DOI:https://doi.org/10.1021/ja00404a037· OSTI ID:6461678
The photolyses of 1,2-diphenyl-2-methyl-1-propanone (1) and its D-, /sup 13/C-, and alkyl-substituted derivatives 2 to 5 in various micellar solutions have been investigated. It was found that the extent of cage disproprotionation to yield benzaldehydes 6 and ..cap alpha..-methylstyrenes 7 is enhanced by a factor of about 10 compared to the photolyses in homogeneous organic solvents. The advantage of using micelles rather than homogeneous solutions to enhance the magnitude of magnetic isotope and magnetic field effects on cage disproportionation is demonstrated. The results are interpreted in terms of a mechanism involving the competition between hyperfine-induced intersystem crossing of a triplet radical pair (/sup 3/RP) to form a singlet radical pair (/sup 1/RP) and escape of /sup 3/RP from the micelle.
Research Organization:
Columbia Univ., New York, NY
OSTI ID:
6461678
Journal Information:
J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 103:14; ISSN JACSA
Country of Publication:
United States
Language:
English