MECHANISMS OF PHOTOELIMINATION REACTIONS OF ALKYL BENZOHYDROXAMATES |
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| Authors: | James Elver Johnson Mohammad Arfan Richard Hodzi Lyman R. Caswell Susan Rasmussen |
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| Affiliation: | Department of Chemistry, Texas Woman's University, Denton, TX 76204, USA |
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| Abstract: | Abstract— Photolysis at 254 nm of alkyl benzohydroxamates [C, H, CONHOR: R = CH3 H2CH3 CH(CH3)2, CH2C6H5 CH(CH3)C2H5 CH(CH3)- n -C6H13] in acetonitrile or hydrocarbon solvents gives benzamide. These reactions can be sensitized by benzophenone (at ca. 350 nm) and are quenched by cis-piperylene. Racemization occurred when 2-octyl (+)-benzohydroxamate was irradiated in cyclohexane. These results are consistent with a mechanism involving a triplet biradical. Photolysis of phenyl benzohydroxamate [C6H5CONHOC6H5] and benzyl N -methylbenzohydroxamate [C6H5CON-(CH3)OCH2Q6H5] cannot be quenched with ris-piperylene and appear to be singlet reactions. |
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