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Phenyl chlorothionoformate has been used in stereo directed synthesis of optically active, (-)-mintlactone, synthesis of peptide α-thioesters having a variety of C-terminal amino acids, synthesis of scyllo-inositol derivatives, thionocarbonylation of unprotected thymine nucleosides, preparation of phenoxythiocarbonyl esters of protected ribonucleosides. It is also used as a reagent in the thionocarbonylation of unprotected thymine nucleosides. It forms phenoxythiocarbonyl esters of protected ribonucleosides which can be reduced by tributyltin hydride to deoxyribonucleosides.
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.
DS Millan.; RH Prager. The dealkylation of tertiary aliphatic amines with phenyl chlorothionoformate. Tetrahedron letters. 199839(24) , 4387-4390.
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):
Similarly, amides are dehydrated to nitriles, and formamides to isonitriles under mild conditions: Tetrahedron Lett., 40, 747 (1999).
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).
Reagent for conversion of imidazoles to imidazole-2-thiones: Synlett, 239 (1995).
Reagent, alternative to chloroformates, for dealkylation of tertiary amines: Austral. J. Chem., 52, 841 (1999).
Mentions de danger (UE): H227-H314-H318
Combustible liquid. Causes severe skin burns and eye damage. Causes serious eye damage.
Mentions de prudence: P280-P305+P351+P338-P309-P310a
Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER/doctor