92387-07-0Relevant academic research and scientific papers
Photosensitized electron transfer oxidation of sulfides: A steady-state study
Bonesi, Sergio M.,Fagnoni, Maurizio,Albini, Angelo
scheme or table, p. 2612 - 2620 (2009/04/05)
The photosensitized electron-transfer oxidation of a series of ethyl sulfides RSEt (1, R = C12H25; 2, PhCH2CH 2; 3, PhCH2; 4, PhCMe2; 5, Ph2CH) has been examined in acetonitrile and the product distribution discussed on the basis of the mechanisms proposed. In nitrogen-flushed solutions, cleaved alcohols and alkenes are formed, whereas under oxygen, in reactions that are 10-70 times faster, sulfoxides and cleaved aldehydes and ketones are formed in addition to the afore-mentioned products. Two sensitizers are compared, 9,10-dicyanoanthracene (DCA) and 2,4,6-triphenylpyrylium tetrafluoroborate (TPP+BF4-), the former giving a higher proportion of the sulfoxide, the latter of cleaved carbonyls. The sulfoxidation is due to the contribution of the singlet oxygen path with DCA. Oxidative cleavage, on the other hand, occurs both with DCA and with TPP+ which is known to produce neither singlet oxygen nor the superoxide anion. This process involves deprotonation from the α position of the sulfide radical cation, but the TPP+ results suggest that O2.- is not necessarily involved and non-activated oxygen forms a weak adduct with the radical cation promoting α-hydrogen transfer, particularly with benzylic derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Synthesis of vicinal bis(alkylthio) derivatives by reductive coupling of dithioacetals derived from aromatic aldehydes with low valent titanium iodide species
Yoshimura, Naritoshi,Igarashi, Koji,Funasaka, Setsuo,Mukaiyama, Teruaki
, p. 640 - 641 (2007/10/03)
Reduction of dithioacetals derived from aromatic aldehydes with low valent titanium iodide species in situ formed by treatment of titanium(IV) iodide with zinc in a mixed solvent of dichloromethane and pivalonitrile at room temperature afforded coupling products, vicinal bis(alkylthio) derivatives, in good to high yields.
The Formation of 1,2-Bis(alkylthio)-1,2-diphenylethanes by the Lithium Diisopropylamide-induced Fragmentation of Dibenzyl Disulfide Followed by the Trapping with Some Alkyl Halides
Ikehira, Hideyuki,Tanimoto, Shigeo
, p. 1423 - 1424 (2007/10/02)
It was found that dibenzyl disulfide undergoes lithium diisopropylamide-induced fragmentation to afford several intermediate species which, on trapping with alkyl halides, lead to the formation of 1,2-bis(alkylthio)-1,2-diphenylethanes and α-alkylbenzyl alkyl sulfides.
