22598-79-4Relevant academic research and scientific papers
JandaJel as a polymeric support to improve the catalytic efficiency of immobilized-1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditions
Lanari, Daniela,Ballini, Roberto,Bonollo, Simona,Palmieri, Alessandro,Pizzo, Ferdinando,Vaccaro, Luigi
supporting information; experimental part, p. 3181 - 3186 (2011/12/04)
JandaJel, with its greater spacing between the linear polymeric chains compared to that of polystyrene matrices, is a very efficient support for improving the catalytic efficiency of TBD under SolFC. The Royal Society of Chemistry.
NaOH-promoted thiolysis of oxiranes using 2-[bis(alkylthio)methylene]-3- oxo-N-o-tolylbutanamides as odorless thiol equivalents
Yu, Haifeng,Dong, Dewen,Ouyang, Yan,Wang, Yan,Liu, Qun
, p. 151 - 155 (2008/03/13)
A convenient and efficient protocol for the thiolysis of oxiranes using 2-[bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides as thiol equivalents has been developed. Promoted by sodium hydroxide (NaOH) in ethanol at room temperature, the cleavage commences and the generated thiolate anions undergo nucleophilic addition in situ. β-Hydroxy Sulfides were obtained in high yields along with good β-regioselectivity, and trans β-hydroxy Sulfides were also isolated. The thiolysis of one α,β-epoxyketone product with the thiol equivalents was accomplished to afford the corresponding α-carbonyl sulfides in excellent yields. In all the cases, 3-oxo-N-o-tolylbutanamide, the precursor of the thiol equivalents, could be recovered in the novel thiolysis process as a byproduct in good yield. Georg Thieme Verlag Stuttgart.
Indium(I) iodide promoted cleavage of dialkyl disulfides - Application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides
Ranu, Brindaban C.,Mandal, Tanmay
, p. 762 - 770 (2007/10/03)
Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions that then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters, and nitriles under neutral conditions producing corresponding β-ketosulfides or β-cyanosulfides. This strategy has also been used for the regioselective nucleophilic ring opening of epoxides by thiolate anions in presence of indium(III) chloride producing corresponding β-hydroxyphenyl sulfides. The reactions are in general, very clean, high yielding, and reasonably fast. Thus, simple and convenient procedures for the synthesis of β-ketosulfides or β-cyanosulfides and β-hydroxyalkyl sulfides have been developed using this cleavage reaction.
CERIC AMMONIUM NITRATE, AN EFFICIENT CATALYST FOR MILD AND SELECTIVE OPENING OF EPOXIDES IN THE PRESENCE OF WATER THIOLS AND ACETIC ACID
Iranpoor, N.,Baltork, Mohammadpour I.,Zardaloo, F. Shiriny
, p. 9861 - 9866 (2007/10/02)
Ring opening of epoxides with catalytic amounts of Ce(IV) as ceric ammonium nitrate (CAN) are performed efficiently in the presence of water, thiols and acetic acid under mild conditions.The epoxides are opened with high regio-and stereoselectivity and with good to excellent yields.The products formed from the reaction of polar substituted epoxides in acetic acid were found to be derivative of succinic acid diester.The mechanism of the reaction is believed to be a radical type, involving the formation of an epoxonium radical cation.
