Journal of the Chemical Society. Perkin transactions I p. 977 - 983 (1981)
Update date:2022-08-04
Topics:
Goosen, Andre
McCleland, Cedric W.
Treatment of a series of 2-substituted-4,4,5,5-tetramethyl-1,3-dioxolanes with iodine monochloride afforded the appropriate 2-substituted-4,4,5,5-tetramethyl-1,3-dioxolan-2-ylium dichloroiodate(I) salts in excellent yields.In contrast to the stable 2-aryl-substituted salts, the 2-alkyl and unsubstituted derivatives were relatively labile.While 2-phenyl-1,3-dioxolan and 2-phenyl-1,3-dioxan afforded low yields of unstable salts,crystalline products could not be isolated from 4,5-disubstituted dioxolans.The reaction was inhibited by electron-withdrawing 4- and 5-substituents.From a study of the effects of photolysis and added iodine, the mechanism is proposed to involve a hydride ion transfer.Possible reasons for the formation of dichloroiodate(I) rather then monohalide salts, are outlined.The stability of the 2-aryl-substituted salts is dicussed in terms of charge distribution in the cation and possible aryl-anion interactions.
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