Preparation of Arylthiocyanates Using N,N′-Dibromo-N,N′-bis(2,5-dimethylbenzenesulphonyl) ethylenediamine and N,NDibromo-2,5-dimethylbenzenesulphonamide in the Presence of KSCN as a Novel Thiocyanating Reagent 英文参考文献.docVIP
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Preparation of Arylthiocyanates Using N,N′-Dibromo-N,N′-bis(2,5-dimethylbenzenesulphonyl) ethylenediamine and N,NDibromo-2,5-dimethylbenzenesulphonamide in the Presence of KSCN as a Novel Thiocyanating Reagent 英文参考文献
Molecules 2001, 6, 253–257
molecules
ISSN 1420-3049
Preparation of Arylthiocyanates Using N,N′-Dibromo-N,N′-
bis(2,5-dimethylbenzenesulphonyl) ethylenediamine and N,N-
Dibromo-2,5-dimethylbenzenesulphonamide in the Presence of
KSCN as a Novel Thiocyanating Reagent
Ardeshir Khazaei*, Abdolhamid Alizadeh and Ramin Ghorbani Vaghei
Department of Chemistry, Faculty of Science, Bu-Ali-Sina University, PIN-65175, Hamadan, Iran
* Author to whom correspondence should be addressed; e-mail a_khazaei@basu.ac.ir
Received: 3 December 2000; in revised form 29 December 2000 / Accepted: 12 December 2000 /
Published: 28 February 2001
Abstract: N-Bromosulphonamides, synthesized via direct bromination of sulphonamides,
react with several types of arene substrates in the presence of KSCN to afford aryl
thiocyanates. The method appears to be generally applicable to benzenoid substrates with
a wide range of substituents, such as N,N-dimethylaniline, p-xylene, anisole, mesitylene
and cumene.
Keywords: KSCN, novel thiocyanation, reagents, synthesis
Introduction
Direct introduction of sulfur into aromatic rings is an interesting objective. Two general strategies
are commonly utilized for this purpose: sulfonation and thiocyanation. Though the latter would be
more useful for our purpose, electrophilic thiocyanation methods described so far are often limited in
scope [1], their main disadvantages being that the reagents used are either highly toxic or present
serious disposal problems (or both).
Molecules 2001, 6
254
The rather unstable thiocyanogen, (SCN)2, has often been used, generated usually in situ from
copper or lead thiocyanates [2-4] or from molecular bromine and an alkali metal thiocyanate [1a].
Procedures involving the somewhat more reactive thiocyanogen chloride or iodide, XSCN, have also
been described [3,5]. These methods call for the use of molecular halogen as co-reagent, or call for
other sources
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