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Phenoxythiocarbonylation and Deoxygenation of Aryl Trifluoromethyl Carbinols
Final rept. Oct 1992-Jun 1993
EDGEWOOD RESEARCH DEVELOPMENT AND ENGINEERING CENTER ABERDEEN PROVING GROUND MD
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Methods for the selective replacement of the OH group by H are very useful in organic transformations and the preparation of biologically active compounds. The most commonly used method for deoxygenation is the catalytic reduction under acidic conditions. However, deoxygenation does not take place when CF3 is attached at the. benzylic carbon. This could be due to the electron- withdrawing property of CF3, which destabilizes the carbonium ion intermediate. Thus, free radical reactions were selected for reductive cleavage of the C-0 Bond. The thiocarbonylation of secondary alcohols and tertiary alcohols carrying an imidazole moiety at the 4-position, followed by the homolytic deoxygenation, yields the deoxygenated products in good yield. Alpha-adrenergic drugs, Phenylthiocarbonylation, Deoxygenation of alcohols.
APPROVED FOR PUBLIC RELEASE