105584-81-4Relevant academic research and scientific papers
Reactions between Grignard Reagents and Thiocarbonyl Compounds: A Revisitation
Alberti, Angelo,Benaglia, Massimo,Macciantelli, Dante,Marcaccio, Massimo,Olmeda, Antonio,Pedulli, Gian Franco,Roffia, Sergio
, p. 6309 - 6315 (2007/10/03)
The radical anions from thiobenzophenone, thiobenzoyltriphenylsilane, and 3,5-di-tert-butylthio- benzoyltriphenylsilane were detected by EPR spectroscopy when these compounds were reacted with a number of Grignard reagents, RMgBr. The radical adducts resulting from addition of R radicals to the thiones were also detected. The formation of the radical anions indicates unambiguously the occurrence of a SET process which might be the initial stage of these reactions. In the case of tris(trimethylsilyl)ethanethial only the radical adducts were detected. The first reduction potentials of these thiones have also been measured in order to verify the feasibility of the SET process. In agreement with the EPR experiments, the calculated standard free energy changes suggest that electron transfer is possible in the first three cases and disfavored with the thioaldehyde.
Synthesis and Chemical Behaviour of Thioacylsilanes (Silyl Thioketones). Part 1. Oxidation to S-Oxides, Conversion into Silylated Thiiranes, Silylated Triarylethylenes, and α-Silylated Sulphides
Barbaro, Gaetano,Battaglia, Arturo,Giorgianni, Patrizia,Maccagnani, Gaetano,Macciantelli, Dante,et al.
, p. 381 - 386 (2007/10/02)
Trimethylsilyl and triphenylsilylaryl thioketones have been synthesized by acid catalysed reaction of the corresponding ketones with hydrogen sulphide.Such silylated thioketones heve been oxidized to give S-oxides and converted with diaryldiazomethanes into triaryl thiiranes; upon treatment with organolithium nucleophiles they undergo thiophilic addition.The ready desulphurization with triphenylphosphine of silylated thiirans to the corresponding silyl triaryl ethylenes is also reported.
