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.
Alkylation of potassium p‐nitrobenzohydroxamate with 1,4‐dibromobutane gave 2‐(p‐nitrobenzoyl)tetrahydro‐2H‐1,2‐oxazine (3). The X‐ray crystal structure of 3 has been determined. The crystals are monoclinic, space group P21/n with a = 6.749(1), b = 7.644(1), c = 21.557(2)Å, β = 98.89(1), V = 1098.8(2)Å3 and Z = 4. The structure, which was refined to R = 0.039 using 1340 observed reflections, shows the oxazine and carbonyl oxygen atoms trans to each other. Alkylation of potassium benzohydroxamate with 1,3‐dibromobutane gave a mixture of 3‐methyl‐2‐benzoyloxazolidine (4) and 5‐methyl‐2‐benzoyloxazolidine (5). The 1H and 13C nmr spectra of the mixture of 4 and 5 indicates that these cyclic hydroxamates exist predominantly in the s‐trans conformation.
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