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Communication | Special issue | Vol 11, No. 1, 1978, pp.105-108
Published online, 1st January, 1970
DOI: 10.3987/S(N)-1978-01-0105
Kinetics of 1,3-Dipolar Cycloaddition Reactions of Aryl - and Diaryldiazomethanes

Rolf Huisgen* and Jochen Geittner

*Institut für Organische Chemie, Universität München, Karlstrasse 23, D-80333 München, Germany

Abstract

The cycloadditions of diazomethane and its aryl derivatives to olefins ore HO(1,3-dipole) — LU(dipolarophile) controlled. Accordingly, electron-attracting substituents in the dipolarophile or electron-releasing substituents in diazomethane accelerate the addition. The log K2 for the reactions of substituted phenyldiazomethanes with ethyl acrylate and norbornene obey Hammett relations with ρ = -1.5 and -0.8. Substituents influence the rate constants of diphenyldiazomethane less.