56504-14-4Relevant academic research and scientific papers
Correlation of thione-to-thiol rearrangement rates of xanthates with solvent scales. Analysis of the reaction behavior by the kamlet-taft parameters, π*, α and β
Eto, Masashi,Tajiri, Okiyasu,Nakagawa, Hidetoshi,Harano, Kazunobu
, p. 8009 - 8014 (2007/10/03)
The thione-to-thiol rearrangement rates for O-(2-alkenyl) (1a- c), O-(1-cyclopropylethyl) (1d) and O-(2-methylthioethyl) (1e) S- methyl xanthates were analyzed by the Kamlet-Taft equation. The results indicate that solvent polarity and solvent hydrogen-bo
Retro-ene type fragmentation of allylic dithiolcarbonates
Eto, Masashi,Nishimoto, Mitsuhiro,Kubota, Shoji,Matsuoka, Toshikazu,Harano, Kazunobu
, p. 2445 - 2448 (2007/10/03)
The formation of 2-alkenyl alkyl sulfides from S-(2-alkenyl) S-alkyl dithiocarbonates with extrusion of COS was found to be effectively catalyzed by Lewis acids. The ab initio calculations strongly suggested that the reaction falls into category of 'retro-alkylthio-ene' reaction.
Potassium fluoride on alumina: One-pot synthesis of S-allyl-S-methyldithiocarbonates by tandem condensation-alkylation-sigmatropic rearrangement
Villemin,Hachemi
, p. 2311 - 2318 (2007/10/02)
Allyl alcohols adsorbed on Al2O3-KF at room temperature reacted wit carbon disulfide and iodomethane and gave S-allyl-S-methyldithiocarbonate. Linalool did not give a rearrangement product. With chrysanthemyl alcohol, opening of the cyclopropane ring was observed.
Stereoselective formation of allylic sulfides via two sequential [3,3]-sigmatropic rearrangements of allylic xanthates and its mechanistic aspects
Harano,Ohizumi,Misaka,Yamashiro,Hisano
, p. 619 - 624 (2007/10/02)
O-(2-Alkenyl) S-alkyl dithiocarbonates (allylic xanthates) were pyrolyzed to give 2-alkenyl alkyl sulfides (allylic sulfides) via the corresponding allylically isomeric S-(2-alkenyl) S-alkyl dithiocarbonates. The reaction follows the first-order rate law
Solvolytic Behavior of O-(1-Cyclopropylethyl) S-Methyl Dithiocarbonate and Related Compounds
Harano, Kazunobu,Kiyonaga, Hideo,Hisano, Takuzo
, p. 1388 - 1396 (2007/10/02)
O-(1-Cyclopropylethyl) S-methyl dithiocarbonate (Ib) was solvolyzed in various solvents to give S-(1-cyclopropylethyl) S-methyl dithiocarbonate (IIb) quantitatively.The reaction obeyed the first-order rate law and the rates were considerably affected by t
A CONVENIENT AND STEREOSELECTIVE SYNTHESIS OF ALLYLIC SULFIDES
Harano, Kazunobu,Ohizumi, Norihide,Hisano, Takuzo
, p. 4203 - 4206 (2007/10/02)
The fractional distillation of O-(2-alkenyl or 2-cycloalkenyl) S-alkyl dithiocarbonates (xanthates) affords 2-alkenyl or 2-cycloalkenyl alkyl sulfides.The reaction involves the -sigmatropic rearrangement of the xanthates to produce S-(2-alkenyl or 2-cycloalkenyl) S-alkyl dithiocarbonates followed by extrusion of carbon oxysulfide to give 2-alkenyl or 2-cycloalkenyl alkyl sulfides.
