Bulletin of the Chemical Society of Japan

Direct conversion of arylamines to the corresponding halides, biphenyls, and sulfides with t-butyl thionitrate.

S Oae, K Shinhama, YH Kim

Index: Oae, Shigeru; Shinhama, Koichi; Kim, Yong Hae Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 7 p. 2023 - 2026

Full Text: HTML

Citation Number: 16

Abstract

t-Butyl thionitrate have been found to be an excellent diazotizing reagent of arylamines in aprotic nonpolar media, affording eventually such products as aryl chlorides, aryl bromides, aryl iodides, biphenyls, and aryl methyl sulfides in the presence of CCl 4, CHBr 3, I 2, benzene, and dimethyl disulfide, respectively, via extrusion of N 2.

 Related Synthetic Route

~%

Detail

~%

Detail

~%

Detail

~%

Detail

~39%

~37%

~24%

~27%

~86%

~%

Detail

~%

Detail

~34%

~59%

~%

Detail

~%

Detail

~%

Detail

~75%

~%

Detail