Journal of the American Chemical Society

Nature of the carbonium ion. I. The. pi.-route to a norbornyl cation from a thiocyanate-isothiocyanate isomerization

LA Spurlock, WG Cox

Index: Spurlock,L.A.; Cox,W.G. Journal of the American Chemical Society, 1969 , vol. 91, # 11 p. 2961 - 2967

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Citation Number: 11

Abstract

Abstract: 2-(A3-Cyclopenteny1) ethyl thiocyanate was isomerized to a mixture of exo-2- norbornyl thiocyanate, ex0-2-norbornyl isothiocyanate, and 2-(A3-~ yclopentenyl) ethyl isothiocyanate in a variety of solvents. No endo-norbornyl products were detected. The rate of reaction and product composition were directly governed by the solvent employed. The necessity of the double bond for isomerization was established by the failure of the ...