Cyclization of the N-butyl-5-methyl-1-hex-4-enaminyl radical and the use of N-lithio-N-butyl-5-methyl-1-hex-4-enamine as a mechanistic probe for electron-transfer …

M Newcomb, MT Burchill

Index: Newcomb, Martin; Burchill, Michael T. Journal of the American Chemical Society, 1983 , vol. 105, # 26 p. 7759 - 7760

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Citation Number: 15

Abstract

When oxaziridine 9 was treated with an excess of lithium amide 1, we observed formation of pyrrolidine 4 (Table 11). This implicates aminyl radical 2 as an intermediate in the reaction and strongly suggests that an electron-transfer step occurred. The last column in Table I1 is the ratio of the moles of pyrrolidine 4 formed in the reactions to the moles of 10 formed. 8 Despite the scatter, the consistency of this ratio leads us to believe that lithium amide ...