2211-89-4Relevant articles and documents
Controlled oxidation of organic sulfides to sulfoxides under ambient conditions by a series of titanium isopropoxide complexes using environmentally benign H2O2 as an oxidant
Panda, Manas K.,Shaikh, Mobin M.,Ghosh, Prasenjit
experimental part, p. 2428 - 2440 (2010/06/18)
Controlled oxidation of organic sulfides to sulfoxides under ambient conditions has been achieved by a series of titanium isopropoxide complexes that use environmentally benign H2O2 as a primary oxidant. Specifically, the [N,N′-bis(2-oxo-3-R1-5-R2- phenylmethyl)-N,N′-bis(methylene-R3)-ethylenediamine]Ti(O iPr)2 [R1 = t-Bu, R2 = Me, R 3 = C7H5O2 (1b); R1 = R2 = t-Bu, R3 = C7H5O2 (2b); R1 = R2 = Cl, R3 = C7H 5O2 (3b) and R1 = R2 = Cl, R 3 = C6H5 (4b)] complexes efficiently catalyzed the sulfoxidation reactions of organic sulfides to sulfoxides at room temperature within 30 min of the reaction time using aqueous H2O 2 as an oxidant. A mechanistic pathway, modeled using density functional theory for a representative thioanisole substrate catalyzed by 4b, suggested that the reaction proceeds via a titanium peroxo intermediate 4c′, which displays an activation barrier of 22.5 kcal mol-1 (ΔG?) for the overall catalytic cycle in undergoing an attack by the S atom of the thioanisole substrate at its σ*-orbital of the peroxo moiety. The formation of the titanium peroxo intermediate was experimentally corroborated by a mild ionization atmospheric pressure chemical ionization (APCI) mass spectrometric technique. The Royal Society of Chemistry 2010.
A General and Expeditious One-Pot Synthesis of Sulfoxides in High Optical Purity from Norephedrine-Derived Sulfamidites
Ruano, Jose L. Garcia,Alemparte, Carlos,Aranda, M. Teresa,Zarzuelo, Maria M.
, p. 75 - 78 (2007/10/03)
A general and simple procedure for preparing any kind of enantiomerically enriched sulfoxide starting from norephedrine-derived N-benzyloxycarbonylsulfamidite 3a is reported. After one-pot reaction of 3a with RMgX, HBF4, and R'MgX, a variety of sulfoxides 6 are obtained in ee usually higher than 93% and isolated yields ranging between 50 and 78%. The obtained configuration is tunable by simply electing the order of the addition of the reagents.
ASYMMETRIC NITROGEN. 71.* GEMINAL SYSTEMS. 45.* N-HALOOXAZIRIDINES
Varlamov, S. V.,Shustov, G. V.,Shibaev, A. Yu.,Puzanov, Yu. V.,Chervin, I. I.,Kostyanovskii, R. G.
, p. 793 - 800 (2007/10/02)
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