59277-53-1Relevant academic research and scientific papers
Nickel(0) triethyl phosphite complex-catalyzed allylic substitution with retention of regio- and stereochemistry
Yatsumonji, Yasutaka,Ishida, Yusuke,Tsubouchi, Akira,Takeda, Takeshi
, p. 4603 - 4606 (2008/03/12)
(Chemical Equation Presented) Nickel(0) triethyl phosphite complex-promoted reaction of allylic acetates with thiols produced allylic sulfides with retention of configuration without allylic rearrangement. A similar reaction of allylic acetates with alcohols and phenols also proceeded with retention of regio- and stereochemistry.
Molecular orbital studies on pericyclic reactions of cinnamyl xanthates in β-cyclodextrin cavities
Eto,Kubota,Nakagawa,Yoshitake,Harano
, p. 1652 - 1659 (2007/10/03)
The solid β-cyclodextrin (β-CyD) complex of O-cinnamyl S-methyl dithiocarbonates (xanthate, 1a), upon heating at 45°C, underwent asymmetric [3,3]-sigmatropic rearrangement to give the optically S-(1-phenylallyl) S-methyl dithiocarbonate (2a) with 60% ee.
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.
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
