Journal of the American Chemical Society

Small-Ring Compounds. XLVII. Reactions of Optically Active Cyclopropylmethylcarbinyl Derivatives1, 2a

M Vogel, JD Roberts

Index: Vogel,M.; Roberts,J.D. Journal of the American Chemical Society, 1966 , vol. 88, # 10 p. 2262 - 2271

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Citation Number: 26

Abstract

Abstract: Cyclopropylmethylcarbinylamine and cyclopropylmethylcarbinol were resolved into optical antipodes and their configurations were related. The former was deaminated with aqueous nitrous acid to give the latter with 0-4 x net inversion of configuration. Solvolysis of N-methyl-4-alkoxypyridinium salts was investigated as a means of providing a leaving group which would not undergo “internal return.” Solvolysis rates for N-methyl-4-(cyclopro- ...