588729-00-4Relevant academic research and scientific papers
A facile [4+1] type synthetic route to thiophenes from dienol silyl ethers and elemental sulfur
Kasano, Yukihiro,Okada, Aoi,Hiratsuka, Daisuke,Oderaotoshi, Yoji,Minakata, Satoshi,Komatsu, Mitsuo
, p. 537 - 542 (2007/10/03)
A facile method for the synthesis of thiophene derivatives via the reaction of readily accessible dienol silyl ethers with elemental sulfur is described. Dienol silyl ethers and elemental sulfur, when heated at 180°C in the presence of MS4A, provided 3-si
1,4-Silatropy of S-α-silylbenzyl thioesters: A convenient route to silyl enol and dienol ethers accompanied by C-C bond formation via thiocarbonyl ylides
Choi, Jinil,Imai, Eiichiro,Mihara, Masatoshi,Oderaotoshi, Yoji,Minakata, Satoshi,Komatsu, Mitsuo
, p. 6164 - 6171 (2007/10/03)
A novel convenient method for the generation of thiocarbonyl ylides from readily accessible starting materials and the first synthetic application of in situ generated ylides in the synthesis of silyl enol and dienol ethers, accompanied by C-C bond formation, is described. Under completely neutral conditions without any catalyst or additive, thermal reactions of S-α-silylbenzyl thioesters in sealed tubes at 180 °C provided silyl enol and dienol ethers in good to excellent yields with high stereoselectivities. This procedure consists of a multistep reaction in a one-pot process, i.e., 1,4-silatropy of S-α-silylbenzyl thioesters to give thiocarbonyl ylides, 1,3-electrocyclization of the ylides to give thiiranes, and the extrusion of sulfur from thiiranes to give silyl enol and dienol ethers.
