Chemistry of N-haloamines. XXIV. Behavior of N, N-dichloroamides and N, N-dichlorocarbamates toward nucleophiles
RE White, P Kovacic
Index: White,R.E.; Kovacic,P. Journal of the American Chemical Society, 1975 , vol. 97, p. 1180 - 1184
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Citation Number: 11
Abstract
Abstract: Exposure of N, N-dichloroamides and N, N-dichlorocarbamates to sodium methoxide or potassium hydroxide in methanol gave moderate to high yields of the corresponding methyl esters and nitrogen gas. The reaction appears to involve chloronitrene (4) as an intermediate via dichloroamide ion (3). The low relative rate of nitrogen evolution from N, N-dichlorourethane (10) vs. rert-butyl N, N-dichlorocarbamate ( ...
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