Phenyl chlorothionoformate, 98+%

General References:

1. DN Kevill.; MJ D'souza. Correlation of the rates of solvolysis of phenyl chlorothionoformate and phenylchlorodithioformate. Canadian journal of chemistry. 199977(5-6) , 1118-1122.
2. DS Millan.; RH Prager. The dealkylation of tertiary aliphatic amines with phenyl chlorothionoformate. Tetrahedron letters. 199839(24) , 4387-4390.
3. Aryl chlorothionoformates react with OH groups to give thiocarbonate esters. These have a much greater tendency to undergo cyclic elimination than their oxygen counterparts, with dehydration as the net result. Thus, e.g. oximes are dehydrated to nitriles under mild conditions: Chem. Commun., 1014 (1970):
4. Similarly, amides are dehydrated to nitriles, and formamides to isonitriles under mild conditions: Tetrahedron Lett., 40, 747 (1999).
5. Alcohols are converted to alkenes in better yields than in the Chugaev (xanthate pyrolysis) method, succeeding with hindered alcohols which do not readily form xanthates: J. Chem. Soc., Chem. Commun., 1215 (1972); Helv. Chim. Acta, 55, 2277 (1972). Secondary alcohols give thiocarbonate esters which can be reduced to alkanes by tributyltin hydride, in a useful deoxygenation sequence. For use in an enantiospecific synthesis of the antiviral agent ganciclovir phosphonate, see: J. Med. Chem., 37, 1371 (1994).
6. Reagent for conversion of imidazoles to imidazole-2-thiones: Synlett, 239 (1995).
7. Reagent, alternative to chloroformates, for dealkylation of tertiary amines: Austral. J. Chem., 52, 841 (1999).