BROMINATION OF <i>tert</i>-BUTYL ESTERS OF 7α-CHLORO AND 7-ALKYLIDENEDEACETOXYCEPHALOSPORANIC ACID SULFONES

Authors

  • М. Ворона Latvian Institute of Organic Synthesis, LV-1006 Riga
  • Г. Вейнберг Latvian Institute of Organic Synthesis, LV-1006 Riga
  • И. Туровский Latvian Institute of Organic Synthesis, LV-1006 Riga
  • Э. Лукевиц Latvian Institute of Organic Synthesis, LV-1006 Riga

DOI:

https://doi.org/10.1007/8307

Keywords:

N-bromosuccinimide, tert-butyl esters of substituted deacetoxycephalosporanic acid sulfones, allylic bromination

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.

How to Cite
Vorona, M.; Veinberg, G.; Turovskis, I.; Lukevics, E.  Chem. Heterocycl. Compd. 2005, 41, 662. [Khim. Geterotsikl. Soedin. 2005, 767.]

For this article in the English edition, see DOI 10.1007/s10593-005-0199-z


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Published

2023-11-15

Issue

No. 5 (2005)

Section

Original Papers