75174-08-2

Upstream product

• 622-42-4 1-nitro-1-phenylmethane 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 94-41-7 benzalacetophenone 
• 588-59-0 stilbene 
• 67765-80-4 (+/-)-1,2-dinitro-1,2-diphenylethane 
• 133683-79-1 4,4-Dimethyl-1-nitro-1-phenyl-pentan-3-one 
• 133683-81-5 4-((Z)-1-tert-Butyl-3-nitro-3-phenyl-propenyl)-morpholine 
• 133683-80-4 4-(5-tert-Butyl-2-oxy-3-phenyl-4,5-dihydro-isoxazol-5-yl)-morpholine 
• 259150-97-5 Methyl 3-phenyl-1,2,4-oxadiazole-5-carboxylate 

Relevant academic research and scientific papers

Metal-Catalyzed Synthesis of Functionalized 1,2,4-Oxadiazoles from Silyl Nitronates and Nitriles

The metal-catalyzed cycloaddition of silyl nitronates and nitriles leading to 1,2,4-oxadiazoles is described. Silver(I) triflate (AgOTf) and and ytterbium(III) triflate [Yb(OTf)3] are suitable catalysts. A variety of functional groups is tolerated in the nitrile. The reaction works well for alkenyl and aryl silyl nitronates while the use of alkyl silyl nitronates is less efficient. Mechanistic studies are in favour of an elimination of tert-butyl(dimethyl)silanol (TBSOH) after the cycloaddition step. The new approach has also been applied for the synthesis of the drug ataluren. (Figure presented.).

SYNTHESIS, PROPERTIES, AND CRYSTAL STRUCTURE OF SILYL NITRONATES (SILYL ESTERS OF ACI-NITROALKANES): TOWARDS THE SN2 REACTION PATH WITH RETENTION OF CONFIGURATION AT SILICON

An efficient and flexible method for the preparation of silyl nitronates is described (see 1-10).NMR. spectral investigations indicate a rapid 1,3-silyl migration process, with an activation energy of about 10 kcal mol-1.X-ray crystallographic