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Communication | Special issue | Vol 10, No. 1, 1978, pp.153-158
Published online, 1st January, 1970
DOI: 10.3987/S-1978-01-0153
Cycloaddition Rates of Diazomethane and Diphenyldiazomethane

Lubor Fisera, Jochen Geittner, Rolf Huisgen,* and Hans-Ulrich Reissig

*Institut für Organische Chemie der Universitat, Karlstraße 23, D - 8000 München 2, Germany

Abstract

Reactivity sequences of dipolarophiles are 1,3-dipole specific. Electron-attracting substituents increase the rate constants of alkenes and alkynes towards diazomethane and diphenyldiazomethane in DMF, whereas electron-releasing substituents decelerate; this is in accordance with a predominant HO(diazoalkane) - LU(dipolarophile) control. The cycloadditions of diazomethane are generally faster and more selective than those of diphenyldiazomethane. Similarly substituted ethylenes and acetylenes do not differ much in their dipolarophilic activity.