PDF herunterladen
Synthesis 2001; 2001(4): 0585-0590
DOI: 10.1055/s-2001-12362
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Improved Procedure to Aryl Thiocyanates: A New Synthetic Application of Dry Arenediazonium o-Benzenedisulfonimides

Margherita Barbero* , Iacopo Degani, Nicola Diulgheroff, Stefano Dughera, Rita Fochi
  • *Dip.to di Chimicia Generale ed Organica Applicata dell'Università, C.so M. D'Azeglio 48, 10125 Torino, Italy; E-mail: fochi@ch.unito.it
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2001 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

Aryl thiocyanates 3 (22 examples) were easily prepared by reaction of dry arenediazonium o-benzenedisulfonimides 1 and sodium thiocyanate (2) in anhydrous acetonitrile at room temperature (20-25 °C) in the presence of copper powder (Procedure A) and at 50 °C or room temperature without the metal catalyst (Procedure B). The yields were from very good to excellent in Procedure A (average yield = 83%), and from modest to excellent in Procedure B (average yield = 63%). In comparison with the thiocyanodediazoniation carried out under traditional Sandmeyer-type conditions, the yields of 3 were higher and the isothiocyanate isomers were formed only in traces. Moreover, the results obtained in the absence of copper confirm the role of the anion of salts 1 as an electron transfer agent.

aryl thiocyanates - thiocyanodediazoniation - stable dry arenediazonium salts