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Synthesis 2001; 2001(4): 0585-0590
DOI: 10.1055/s-2001-12362
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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
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Publication Date:
31 December 2001 (online)

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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