New syntheses of aryl isothiocyanates†

T Besson, J Guillard, CW Rees, V Thiéry

Index: Besson, Thierry; Guillard, Jerome; Rees, Charles W.; Thiery, Valerie Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 5 p. 889 - 892

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Citation Number: 40

Abstract

Primary aromatic amines are readily converted into arylimino-1, 2, 3-dithiazoles 2 and the derived cyanothioformanilides 6, both of which are rapidly cleaved by ethylmagnesium bromide in hot THF to give the corresponding isothiocyanates. The transformation 2→ 6→ ArNCS can be performed as a 'one-pot'operation. The imines 2 are also converted, more slowly, into the isothiocyanates by sodium hydride in hot THF, via the ...