Issue 6, 1991

The regioselectivity of cycloaddition reactions between diazomethane and 3-vinylcephalosporins

Abstract

Diphenylmethyl (6R,7R)-7-phenylacetamido-3-vinylceph-3-em-4-carboxylate 1 undergoes regioselective addition of diazomethane to give the 1-pyrazoline 7, which readily undergoes thermolysis to give the cyclopropyl analogue 10. The regioselectivity is reversed, however, when one or more electron withdrawing ester substituents are attached to the 3-vinyl group.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1991, 1361-1364

The regioselectivity of cycloaddition reactions between diazomethane and 3-vinylcephalosporins

S. C. M. Fell, M. J. Pearson, G. Burton and J. H. Bateson, J. Chem. Soc., Perkin Trans. 1, 1991, 1361 DOI: 10.1039/P19910001361

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