Abstract
The reaction of both, (1-methylcyclopropyl)carbinyl mesylate and 1-methylcyclobutyl mesylate, with NaBH 4 in aqueous diglyme affords a mixture of 1,1-dimethylcyclopropane and methylcyclobutane in addition to 1-methylcyclobutanol. The hydrolysis of both mesylates resulted in the formation of only one product, i.e. 1-methylcyclobutanol. The results obtained when the amounts of BH 4 - and water were varied indicate that the reaction of the primary mesulate with NaBH 4 proceeds by two competitive mechanisms (S N 1 and S N 2). The results are rationalized in terms of nonclassical ions and the inadequacy of the equilibrating classical ion pair hypothesis is discussed. The suggestion is made that the described method might be of use in some cases for distinguishing between classical and nonclassical carbonium ions.
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