The acid catalyzed ring expansion (1) of penicillin sulfoxide esters, 1, to deacetoxy cephalosporins, 2, has assumed added importance due to the demonstrated oral effectiveness of the broad-spectrum antibiotic, cephalexin (2). We now wish to report additional studies that further aid in elucidating
The determination of stereochemistry and reactions of 3-hydroxy, 3-methyl cephalosporins
β Scribed by Gerald E. Gutowski; Cecelia M. Daniels; R.D.G. Cooper
- Publisher
- Elsevier Science
- Year
- 1971
- Tongue
- French
- Weight
- 198 KB
- Volume
- 12
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
In the preceding communication (l), we reported the facile preparation of a novel class of cephalosporins, 3-hydroxy-3-methyl-cepham derivatives, I, via acid catalyzed ring expansion of penicillin sulfoxides.
This communication describes some additional chemical and spectroscopic properties of these compounds, and thus establishes the 2 configuration at C3 (i.e., 3B-hydroxyl).
π SIMILAR VOLUMES
In the previous communications, 1,2) we reported the facile syntheses of a novel class of cephalosporlns, 3-methylenecepham derivatives, by an electrochemical reduction or chromium(I1) salts reduction of cephalosporanic acids. This communication describes some aspects of chemical reactions of these
## Abstract The enol of acetone, formed by disproportionation reactions of 1βhydroxyβ1βmethylethyl radicals, is detected by NMR, spectroscopy during photoreactions of 3βhydroxyβ3βmethylβ2βbutanone in acetonitrile and of acetone in 2βpropanol and slowly tautomerizes to acetone. The photolysis of 3βh