95416-99-2Relevant academic research and scientific papers
Continuous Flow Synthesis of 2H-Thiopyrans via thia-Diels–Alder Reactions of Photochemically Generated Thioaldehydes
Sachse, Florian,Gebauer, Konrad,Schneider, Christoph
supporting information, p. 64 - 71 (2020/11/30)
Herein, we report a novel protocol for the photochemical generation of thioaldehydes in a continuous flow process which were in situ reacted with electron rich 1,3-butadienes in thia-Diels–Alder reactions. A broad range of 3,6-dihydro-2H-thiopyrans were formed as products in much higher yields and productivities as compared to classical batch processes. Moreover, greatly reduced reaction times and a facile large-scale preparation of products were achieved by fully exploiting the advantages of continuous flow technology.
Protiodesilylation of 3-trimethylsilyl-2-thiabicyclo[2.2.1]hept-5-enes and derivatives: A stereochemical study
Bonini, Bianca F.,Masi, Enza,Masiero, Stefano,Mazzanti, Germana,Zani, Paolo
, p. 3553 - 3562 (2007/10/03)
endo- and exo-trimethylsilyl-3-phenyl-2-thiabicyclo[2.2.1]hept-5-enes, the endo-trimethylsilyl-exo-S-oxide and their S,S-dioxide derivatives were protiodesilylated with fluoride ion. Stereoconvergent reactions were found, affording the endo-phenyl derivatives. These results can be rationalised with the hypothesis of a common carbanionic intermediate. In contrast, the desilylation of 3-endo-trimethylsilyl-3-exo-phenyl-2-thiabicyclo[2.2.1]heptane gave a mixture of endo- and exo-isomers, thus proving the involvement of the double bond in the control of the reaction stereoselectivity.
STEREOCHEMISTRY OF PROTIODESILYLATION OF 3-TRIMETHYLSILYL-2-THIABICYCLOHEPTENES, HEPTANES AND DERIVATIVES.
Bonini, Bianca Flavia,Masi, Enza,Masiero, Stefano,Mazzanti, Germana,Zani, Paolo
, p. 379 - 380 (2007/10/02)
Some 3-trimethylsilyl-2-thiabicycloheptenes and heptanes of known configuration were protiodesilylated and the stereochemistry of the reaction was studied.Evidences for a carbanionic intermediate as well as the pivotal role played by the metal coun
GENERATION OF THIOALDEHYDES VIA FLUORIDE INDUCED ELIMINATION OF Α-SILYLDISULFIDES
Krafft, Grant A.,Meinke, Peter T.
, p. 1947 - 1950 (2007/10/02)
A mild, efficient and general method for the generation of reactive thioaldehydes from α-silyldisulfides is described.
Transformation of Thiosulphonates into α-Sulphonyldisulphides, a New Class of Thioaldehyde Precursors
Kirby, Gordon W.,Lochead, Alistair W.,Sheldrake, Gary N.
, p. 1469 - 1470 (2007/10/02)
Toluene-p-thiosulphonates, RCH2SSO2Tol (1) where R is an electron-withdrawing group, are transformed readily into α-sulphonyldisulphides (2) which, with triethylamine, undergo fragmentation-elimination to give 2 moles of thioaldehydes, RCHS.
