Base-induced fragmentation of. beta.-hydroxy nitrosamines

RN Loeppky, WA McKinley, LG Hazlitt…

Index: Loeppky, R. N.; McKinley, W. A.; Hazlitt, L. G.; Outram, J. R. Journal of Organic Chemistry, 1982 , vol. 47, # 25 p. 4833 - 4841

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Citation Number: 5

Abstract

b-Hydroxy nitrosamines have been found to undergo a base-induced fragmentation reaction. The reaction cleaves the C,-C, bond of the substrate to produce an aldehyde or ketone and a smaller alkylnitrosamine. Rate constants for the fragmentation induced by potassium tert-butoxide in THF or tert-butyl alcohol have been measured for nine substrates at temperatures between 35 and 70 OC. The rate constants are a function of base ...