The chemistry of small??ring compounds. Part 47. Small??ring interference in the ozonolysis of cyclopropylidenecycloalkanes

…, A Holland, JC van Velzen, H Steinberg…

Index: Heuvel, C. J. M. van den; Hofland, A.; Velzen, J. C. van; Steinberg, H.; Boer, Th. J. de Recueil: Journal of the Royal Netherlands Chemical Society, 1984 , vol. 103, # 7-8 p. 233 - 240

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Abstract

Abstract Ozonolysis of olefins Ia-c containing a cyclopropylidene group, does not follow the classical Criegee mechanism but gives the anomalous products IIa-c, IIIa-c, IVa-c and Va-c, as outlined in Scheme 2. None of these oxidation products contains the cyclopropyl ring any more. It is suggested that primary ozonides containing a cyclopropyl moiety, undergo already at low temperature simultaneous 0–0 homolysis and small-ring fission, thus ...