74738-01-5Relevant academic research and scientific papers
α-NITRO SULFONES. 2. CONVENIENT NEW SYNTHESIS AND SELECTED FUNCTIONAL GROUP TRANSFORMATIONS
Wade, Peter A.,Hinney, Harry R.,Amin, Nayan V.,Vail, Peter D.,Morrow, Scott D.,et al.
, p. 765 - 770 (2007/10/02)
(Phenylsulfonyl)nitromethane (1) is preferentially C-alkylated by benzylic halides and primary alkyl iodides, affording secondary α-nitro sulfone products. α-Nitro sulfones are also obtained from the corresponding C-alkylation of allylic acetates in the presence of catalytic tetrakis(triphenylphosphine)palladium.The palladium(0)-catalyzed reaction is stereospecific for geranyl and neryl acetates and is also regioselective.Desulfonation of α-nitro sulfones is readily accomplished by light-induced reduction with 1-benzyl-1,4-dihydronicotinamide (BNAH).Reduction of secondary α-nitro sulfones with 20percent aqueous titanium(III) chloride affords nitriles.Oxidation with alkaline permanganate affords carboxylic acids.
C-Alkylation Reactions of Phenylsulfonylnitromethane. A Convenient New α-Nitro-sulfone Synthesis
Wade, Peter A.,Morrow, Scott D.,Hardinger, Steven A.,Saft, Mallory S.,Hinney, Harry R.
, p. 287 - 288 (2007/10/02)
Phenylsulfonylnitromethane (1) is C-alkylated by benzylic halides and primary alkyl iodides affording α-nitro-sulfones in 43-75percent yield; α-nitro-sulfones (83-90percent yield) are also obtained from the corresponding C-alkylation of allylic acetates i
