31356-08-8Relevant academic research and scientific papers
A mild access to chiral syn 1,2-diaryl glycols by stereoselective ring opening of ortho substituted trans 2,3-diaryl-oxiranes using Amberlyst 15 in H2O/THF system
Lupattelli, Paolo,Chiummiento, Lucia,Funicello, Maria,Tramutola, Francesco,Marmo, Antonella,Gliubizzi, Natascia,Tofani, Daniela
supporting information, p. 5662 - 5668 (2015/08/03)
Amberlyst 15 was an efficient and green catalyst for the reaction of 2,3-diaryloxiranes with H2O in organic co-solvent to prepare glycols in high yield. Ortho substituted trans 2,3-diaryloxiranes afforded the corresponding syn glycols stereo- and enantiospecifically. Stereoselectivity appeared related to the coordination ability of the substituents, irrespective of their electronic properties. Indeed o-OCH3 and o-OBn substituted syn glycols were obtained in high stereochemical ratios (6/1 and 10/1, respectively), and o-OTIPS and o-NO2 substituted ones were obtained as exclusive products, with the same ee of the parent epoxides.
L'o-nitrobenzylidenedimethylsulfuranne: synthese, reactivite
Stanc, Yannick Le,Corre, Maurice Le
, p. 2958 - 2960 (2007/10/02)
In aqueous solution, o-nitrobenzyldimethylsulfonium bromide and the corresponding ylid give, depending upon the conditions, o-nitrobenzyl alcohol, o-nitrobenzylsulfide, or methyl o-hydroxymethylbenzyl sulfide.The o-nitrophenyloxiranes may be obtained by the reaction of nitrobenzylidenedimethylsulfurane with aldehydes in a two-phase aqueous sodium hydroxide/dichloromethane system.
