Abstract
The action of N-bromosuccinimide on tert-butyl esters of 7α-chloro- and 7-alkylidenedeacetoxycephalosporanic acid sulfones upon irradiation with visible light leads to the formation of a mixture of the product of allylic bromination of the 3-methyl group, namely, 3-bromomethyldeacetoxycephalosporanate, and the product of replacement of a proton at C(2) in the latter, namely, 2-bromo-3-bromomethyldeacetoxycephalosporanate. Small amounts of E-isomers were also obtained in the case of the Z-isomer of the 7-(4-nitrobenzylidene) derivative. In the case of the 7α-chloro derivative only substitution of one or two protons at C(2) occurs during bromination without irradiation, the same as the isomerization of the double bond in the cepheme system.
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Dedicated to Academician N. K. Kochetkov on the occasion of this ninetieth birthday.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 767–774, May, 2005.
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Vorona, M., Veinberg, G., Turovskis, I. et al. Bromination of tert-Butyl Esters of 7α-Chloro and 7-Alkylidenedeacetoxycephalosporanic Acid Sulfones. Chem Heterocycl Compd 41, 662–667 (2005). https://doi.org/10.1007/s10593-005-0199-z
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DOI: https://doi.org/10.1007/s10593-005-0199-z