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Issue 6, 1978
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N-Iodo-amides: cyclisation of substituted biphenyl-2-carboxamides

Abstract

Homolysis of N-iodo-amides leads to 2′-, 3′-, and 4′-substituted biphenyl-2-carboxamidyl radicals which cyclise intramolecularly to give γ- and δ-lactams in parallel processes. The proportion of Ar1-5 and Ar2-6 cyclised products is in accord with the steric and electronic effects of the substituents. 4′-Iodo-4′-methoxy-N-methyl-3-oxoisoindoline-1-spiro-1′-cyclohexa-2′,5′-dienes have been identified as spiro-intermediates in the cyclisation of N-methyl-4′-methoxybiphenyl-2-carboxamide.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1978, 653-657
Article type
Paper

N-Iodo-amides: cyclisation of substituted biphenyl-2-carboxamides

S. A. Glover and A. Goosen, J. Chem. Soc., Perkin Trans. 1, 1978, 653
DOI: 10.1039/P19780000653

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