Several primary amines 2 have been oxidized with dimethyldioxirane (1) under a variety of conditions. Mixtures of dimeric nitrosoalkanes 4 and oximes 5 were typically obtained with solutions of the oxidant in excess. In several instances, nitrones 12 were found as byproducts in these reactions. In situ oxidations using oxone in buffered aqueous acetone solution also gave nitrosoalkanes 4 and oximes 3 as important products; in addition, oxaziridines 11 were obtained in significant amounts in biphasic procedures containing methylene chloride. The corresponding nitroalkanes 3 were not formed in major amounts in either oxidation procedure, unless large excesses of oxidant were used. These results are discussed in terms of the several competing processes which occur under the different reaction conditions.
Crandall Jack K., Reix Thierry, Tetrahedron Lett, 35 (1994) N 16, S 2513-2516
作者:Crandall Jack K., Reix Thierry
DOI:——
日期:——
Dimethyldioxirane oxidation of primary amines
作者:Jack K. Crandall、Thierry Reix
DOI:10.1021/jo00051a017
日期:1992.12
Several primary amines 2 have been oxidized with dimethyldioxirane (1) under a variety of conditions. Mixtures of dimeric nitrosoalkanes 4 and oximes 5 were typically obtained with solutions of the oxidant in excess. In several instances, nitrones 12 were found as byproducts in these reactions. In situ oxidations using oxone in buffered aqueous acetone solution also gave nitrosoalkanes 4 and oximes 3 as important products; in addition, oxaziridines 11 were obtained in significant amounts in biphasic procedures containing methylene chloride. The corresponding nitroalkanes 3 were not formed in major amounts in either oxidation procedure, unless large excesses of oxidant were used. These results are discussed in terms of the several competing processes which occur under the different reaction conditions.
Oxidative cyclizations of allenic sulfonamides with dimethyldioxirane
作者:Jack K. Crandall、Thierry Reix
DOI:10.1016/s0040-4039(00)77158-9
日期:1994.4
The dimethyldioxiraneoxidations of allenic amine derivatives give highly functionalized nitrogen heterocycles derived from cyclizations of intermediate allene mono- and diepoxides.