96994-48-8Relevant academic research and scientific papers
Reaction of 3-Phenylglycidic Esters. III. Reaction of cis-3-Arylglycidic Esters with Various Thiophenols
Hashiyama, Tomiki,Inoue, Hirozumi,Konda, Mikihiko,Takeda, Mikio
, p. 1256 - 1259 (2007/10/02)
The reaction of the cis-3-arylglycidic esters 2 and 10 with thiophenols (3) has been investigated.The reactivity and stereoselectivity of the oxirane ring-opening of these cis-glycidic esters were lower than those of the trans-analogues (1 and 9).These tendencies were more apparent in the 4-MeO derivative (2).On the other hand, the tin-catalyzed reaction of 2 with 3a was highly stereospecific and afforded the cis-opening products (5a).Keywords - cis-3-arylglycidic ester; thiophenol; oxirane ring-opening; tin catalyst; stereoselectivity
Reaction of 3-Phenylglycidic Esters. Part 2. Stereo- and Regio-selectivity in the Oxirane Ring Opening of Methyl trans-3-(4-Methoxyphenyl)glycidate with Various Thiophenols and the Effects of Solvent and Temperature
Hashiyama, Tomiki,Inoue, Hirozumi,Takeda, Mikio,Aoe, Keiichi,Kotera, Keishi
, p. 421 - 428 (2007/10/02)
The effects of the solvent and temperature on the reaction of the trans-glycidate (1) with various substituted thiophenols (2) in the presence or absence of a catalyst have been investigated.The temperature had a surprisingly large effect on the stereochemistry of the oxirane ring-opening of (1).At room temperature, the erythro-isomer (4) (trans-opening product) was obtained as a major product in the absence of catalyst, while the cis-opening product (3) (threo-isomer) was produced predominantly at higher temperature.On the other hand, in a dipolar aprotic solvent, the regioisomer (5) was formed, the yield increasing with the electron-donating ability of the substituents on (2).The formation of compound (5) may involve single-electron transfer as a key step.
