123311-34-2Relevant academic research and scientific papers
A General, High Yield Synthesis of α-Oxoketene Dithioacetals and O-(1-Alkoxy-2,2-dialkyl)vinyl S-Alkyl Dithiocarbonates from Carboxylic Esters
Ali, Syed Mashhood,Tanimoto, Shigeo
, p. 684 - 685 (1989)
α-Oxoketene dithioacetals (5) and O-(1-alkoxy-2,2-dialkyl)vinyl S-alkyl dithiocarbonates (4) were prepared in high yields from carboxylic esters by the reaction of their lithium enolates (2) with carbon disulphide at -78 deg C followed by alkylation.
Reaction of Lithium Enolates with Carbon Disulfide: Synthesis of O-(1-Alkoxy-2,2-dialkylvinyl) S-Alkyl Dithiocarbonates
Ali, Syed Mashhood,Tanimoto, Shigeo
, p. 5603 - 5607 (2007/10/02)
The reaction of lithium enolates 5, generated from esters 4 having only one α-hydrogen atom, with carbon disulfide at -78 deg C followed by alkylation with alkyl halide afforded O-(1-alkoxy-2,2-dialkylvinyl) S-alkyl dithiocarbonates (7) in excellent yields (84-95percent).An unambiguous structural assignment was made with the help of spectral and microanalytical data.A plausible mechanism has been proposed, in light of available literature, that explains the results of the reaction of enolates with carbon disulfide.The transformation is significant from both the synthetic and mechanistic points of view.These products have not previously been reported, and compound 8 was reported to be the primary product of the reaction of lithium enolate with carbon disulfide.This report represents the first example of formation of a C-O bond between the oxygen of an enolate and the carbon disulfide.
