Canadian Journal of Chemistry

REARRANGEMENT STUDIES WITH 14C: XXIV. SOLVOLYSES OF 2-(α-NAPHTHYL)-1-14C-ETHYL p-TOLUENESULFONATE

CC Lee, AG Forman

Index: Lee,C.C.; Forman,A.G. Canadian Journal of Chemistry, 1965 , vol. 43, p. 3387 - 3391

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Citation Number: 3

Abstract

Acetolysis and formolysis of 2-(α-naphthyl)-1-14C-ethyl p-toluenesulfonate (I-OTs) were interrupted after 50% completion and the products, 2-(α-naphthyl) ethyl acetate and formate (I-OAc and I-OCHO), and the" unreacted" I-OTs were recovered. Rearrangements of the 14C- label from C-1 to C-2 were found to be about 46% and 50%, respectively, in the I-OAc and I- OCHO. A similar rearrangement amounting to about 38% was observed in the I-OTs ...