The reaction of alkyl halides with mercuric thiocyanate in tetrahydrofuran. The solvent incorporation and the intermediacy of O-alkyltetrahydrofuranium ions.

N Watanabe, S Uemura, M Okano

Index: Watanabe,N. et al. Bulletin of the Chemical Society of Japan, 1975 , vol. 48, p. 3205 - 3209

Full Text: HTML

Citation Number: 5

Abstract

The reaction of alkyl halides with mercuric thiocyanate in tetrahydrofuran (THF) affords mainly the THF-incorporated products, R [O (CH 2) 4] n NCS and R [O (CH 2) 4] n SCN (mostly n= 1 and 2), where the isomer ratios (N/S ratios) are nearly 1. The reaction of EtO (CH 2) m Br (m= 2–5) with mercuric thiocyanate in THF or n-Bu 2 O proceeds rapidly only in the case of m= 4 to give EtO (CH 2) 4 NCS and EtO (CH 2) 4 SCN, the N/S ratio being also ...