Journal of the American Chemical Society

The Reaction of 2-Cyclopropylethylamine-1-14C with Nitrous Acid

GE Cartier, SC Bunce

Index: Cartier,G.E.; Bunce,S.C. Journal of the American Chemical Society, 1963 , vol. 85, p. 932 - 937

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Citation Number: 20

Abstract

2-Cy~ lopropylethylamine-l-*~ C reacts with nitrous acid to give, in, 5770 yield, a mixture of 2- cyclopropylethanol, cyclopropylmethylcarbinol and cyclopentanol in relative amounts of 1. OO: O 76: 0.18. The isotope position distribution in these alcohols corresponds to an extensive rearrangement whose predominant feature is an irreversible shift of cyclopropyl from C-2 to C-1, which is uniquely determined by the conformation of the rearranging ion. ...