Exceptionally stable ozonides. Influence of methyl substituents on the course of cyclopentene ozonolyses and on the reactivities of ozonides

…, J Baran, E Will, H Yamakoshi, K Teshima…

Index: Mayr, Herbert; Baran, Janusz; Will, Elfriede; Yamakoshi, Hideyuki; Teshima, Koichi; Nojima, Masatomo Journal of Organic Chemistry, 1994 , vol. 59, # 17 p. 5055 - 5058

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Citation Number: 28

Abstract

Ozonolyses of 1, 2, 3, 3, 4, 4, 5, 5-octamethyl-(la), 1, 2, 3, 3, 4, 4, 5-heptamethyl-(lb), and 1, 2, 3, 3, 4, 4-hexamethyl cyclopentenes (IC) in methanol did not yield the ordinary hemiperacetals but gave the corresponding ozonides 6a-c instead." he ozonides 6a, b were extremely stable and remained intact even when refluxed with triphenylphosphine in tetrahydrofuran. Cycloreversion of the primary ozonides from unsymmetrically substituted ...

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