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Issue 0, 1985
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Cyclodextrin-promoted free-radical dediazoniation of benzenediazonium ions

Abstract

The effect of β-cyclodextrin (β-CD) on the decomposition of benzenediazonium ions is reported. Dediazoniation of substituted benzenediazonium ions (X =p-Me, p-Cl, and p-NO2) is accelerated by β-CD and proceeds via a radical pathway to form XC6H5, irrespective of the nature of the substituent X or the atmosphere (N2 or O2). In contrast, trehalose and permethylated β-CD exhibit no enhancement of rate and reduce the yields of XC6H5. The cyclodextrin-promoted dediazoniation exhibits both saturation kinetics and competitive inhibition. The observations described are explained in terms of a mechanism involving (i) the specific formation of a syn-arylazo ether via an inclusion complex formed between the benzenediazonium ion and β-CD and (ii) subsequent homolytic scission of the syn-arylazo ether.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1985, 991-995
Article type
Paper

Cyclodextrin-promoted free-radical dediazoniation of benzenediazonium ions

K. Fukunishi, J. Hira, H. Yamanaka, M. Nomura and S. Kojo, J. Chem. Soc., Perkin Trans. 1, 1985, 991
DOI: 10.1039/P19850000991

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