34520-64-4Relevant articles and documents
A new selenium catalyzed synthesis of S-Alkyl carbonothioates from alcohols, carbon monoxide, sulfur and alkyl halides
Mizuno, Takumi,Nishiguchi, Ikuzo,Hirashima, Tsuneaki,Ogawa, Akiya,Kambe, Nobuaki,Sonoda, Noboru
, p. 4773 - 4776 (2007/10/02)
Selenium showed excellent catalytic activity for carbonothiolation of alcohols with carbon monoxide and sulfur under mild conditions. S-Alkyl carbonothioates were synthesized in good yields from various alcohols, carbon monoxide, elemental sulfur, and alk
A General Strategy for Elaboration of the Dithiocarbonyl Functionality, -(C=O)SS-: Application to the Synthesis of Bis(chlorocarbonyl)disulfane and Related Derivatives of Thiocarbonic Acids
Barany, George,Schroll, Alayne L.,Mott, Andrew W.,Halsrud, David A.
, p. 4750 - 4761 (2007/10/02)
A variety of sulfenyl chlorides have been reacted with a variety of alkoxythiocarbonyl compounds to give adducts which then lose (spontaneously, or upon thermolysis, or in the presence of Lewis acid catalyst) the alkyl chloride to provide an assortment of dithiocarbonyl compounds in good to excellent yields.The preparations of bis(chlorocarbonyl)disulfane (1), ((trichloromethyl)dithio)carbonyl chloride (2), ((alkoxycarbonyl)dithio)carbonyl chlorides (3 and 4), and (((alkylthio)carbonyl)dithio)carbonyl chlorides (5 and 6) by this methodology were optimized; some of the (alkoxydichloromethyl)disulfanyl adducts, e.g., ROCCl2SS(C=O)Cl (10) and ROCCl2SS(C=O)OR'(54), were reasonable stable and could be isolated.All new compounds were characterized by analytical data, 1H and 13C NMR, IR, UV, and mass spectrometry, and high-yield derivatizations with alcohols or N-methylaniline.The reaction with N-methylaniline was also adapted to a rapid, convenient, and precise analytical-scale assay of mixtures of compounds containing acid chloride and/or sulfenyl chloride functionalities.The kinetics, mechanism, and stereochemistry of the dithiocarbonyl synthesis are discussed.
