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ChemInform Abstract: New Syntheses of Aryl Isothiocyanates
- Source :
- ChemInform. 29
- Publication Year :
- 2010
- Publisher :
- Wiley, 2010.
-
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 cyanothioformanilides 6. Conversion of the anilides 6 into isothiocyanates is much faster under microwave irradiation in 2,6-lutidine. Mechanisms are proposed for these reactions.
Details
- ISSN :
- 15222667 and 09317597
- Volume :
- 29
- Database :
- OpenAIRE
- Journal :
- ChemInform
- Accession number :
- edsair.doi...........b698ba8129138840d19b327f677e28f6