A new selenium catalyzed synthesis of S-Alkyl carbonothioates from alcohols, carbon monoxide, sulfur and alkyl halides
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
SULFUR-ASSISTED O-CARBONYLATION OF ALCOHOLS WITH CARBON MONOXIDE IN THE PRESENCE OF DBU
The first example of sulfur-assisted O-carbonylation is described.Alcohols react with carbon monoxide, elemental sulfur, and alkyl halides in the presence of DBU to give S-alkyl carbonothioates selectively in good to excellent yields.
Triphenylphosphine Decomposition of Sulfenyl Thiocarbonates
Several sulfenyl thiocarbonates (RSSCO2CH3) have been decomposed with triphenylphosphine.In the case of R = alkyl, desulfurization takes place to give the S-alkyl thiocarbonate while in the case of R = aryl, a phosphonium salt is likely formed which on chromatographic workup on silica gel is converted to a thiol and triphenylphosphine oxide and sulfide.A mechanistic interpretation is offered.
Harpp, David N.,Granata, Alessandro
p. 271 - 273
(2007/10/02)
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