35200-02-3Relevant articles and documents
Superoxide ion-promoted facile one-pot synthesis of O-alkyl-S-methyl dithiocarbonates from alcohol under mild reaction conditions
Singh, Satish Kumar,Singh, Krishna Nand
experimental part, p. 94 - 97 (2011/04/16)
A new, mild, and efficient protocol for the one-pot synthesis of O-alkyl-S-methyl dithiocarbonates (xanthates) has been described in reasonably good yields from a variety of alcohols employing carbon disulfide and methyl iodide using superoxide ion at room temperature. Copyright Taylor & Francis Group, LLC.
1-(Methyldithiocarbonyl)imidazole: A Reagent of S-Methyldithiocarbonylation
Sun, Wei Yan,Hu, Ji Qing,Shi, Yong Ping
, p. 1279 - 1280 (2007/10/03)
The development, synthesis and use of the 1-(methyldithiocarbonyl)imidazole as a reactive reagent for the mild conversion of alcohols to O-alkyl, S-methyl dithiocarbonates is reported.
Catalytic Rearrangement of O,S-Dialkyl Dithiocarbonates to S,S-Dialkyl Dithiocarbonates by Pyridine N-Oxides. The Reaction Mechanism
Harano, Kazunobu,Shinohara, Ikuo,Sugimoto, Shin-ichiro,Matsuoka, Toshikazu,Hisano, Takuzo
, p. 576 - 581 (2007/10/02)
The reaction of O-alkyl S-methyl dithiocarbonates (xanthates) (I) with pyridine N-oxides (II) gave the corresponding S-alkyl S-methyl dithiocarbonates (dithiolcarbonate) (III) together with the symmetric S,S-dialkyl and S,S-dimethyl dithiocarbonates in good yields.Pyridine N-oxides bearing electron-donating substituents are efficient catalysts for rearrangement of I to III.The reaction is pseudo-first-order and the apparent first-order rate constant is proportional to the concentration of II.The role of pyridine N-oxides and the reaction behavior of O,S-dialkyldithiocarbonates are discussed on the basis of kinetic and molecular orbital calculation data.The rearrangement may proceed by nucleophilic attack of -SCOSR derived from a complex of I and II on the O-alkyl group of xanthates.The reaction provides a useful preparation method for alkanethiols by aminolysis of the products with ethanolamine.Keywords O,S-dialkyl dithiocarbonate; S,S-dialkyl dithiocarbonate; pyridine N-oxide; thiol; charge transfer; catalytic rearrangement; kinetics; ethanolamine; frontier molecular orbital