The reaction of. OMEGA.-ethoxyalkyl bromides with silver (I) cyanide and nitrite. The participation of an oxonium ion.

N Watanabe, S Uemura, M Okano

Index: Watanabe,N. et al. Bulletin of the Chemical Society of Japan, 1979 , vol. 52, p. 1975 - 1977

Full Text: HTML

Citation Number: 1

Abstract

The reaction of ω-ethoxyalkyl bromides (C n: n= 2–5) with silver (I) cyanide or nitrite in less polar solvents to give the corresponding isocyanide or a mixture of the corresponding alkyl nitrite and nitroalkane respectively, proceeded with ease only when n= 4. In the latter reaction, the ratios of O-and N-attack (O/N) were 16–18/82–84 and 31–46/54–69 when n\ neweq4 and n= 4 respectively. The facile reaction in both cases when n= 4 and the ...