C-Alkylation Reactions of Phenylsulfonylnitromethane. A Convenient New α-Nitro-sulfone Synthesis
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
Wade, Peter A.,Morrow, Scott D.,Hardinger, Steven A.,Saft, Mallory S.,Hinney, Harry R.
Stereospecific Dehydrative Alkylation of Bis-Sulfones: Synthesis of a Lesser Tea Tortrix Pheromone
The intra- and intermolecular condensation of alcohols with bis-sulfone methylenes, i.e., dehydrative alkylation, using DEAD and Ph3P proceeds stereospecifically at room temperature under essentially neutral conditions affording good to excellent yields o
Yu, Jurong,Cho, Hyun-Sung,Falck, J. R.
p. 5892 - 5894
(2007/10/02)
A NEW METHOD FOR THE SYNTHESIS OF SECONDARY α-NITRO SULPHONES
Nitro(phenylsulphonyl)methane was preferentially C-alkylated by different alkyl halides using the PTC technique to produce secondary α-nitro sulphones (2-9) in good yield (65-75percent).
El-Khawaga, Ahmed M.,Ismail, Mohamed T.,Abdel-Wahab, Aboel-Magd A.
p. 235 - 238
(2007/10/02)
α-NITRO SULFONES. 2. CONVENIENT NEW SYNTHESIS AND SELECTED FUNCTIONAL GROUP TRANSFORMATIONS
(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.
Wade, Peter A.,Hinney, Harry R.,Amin, Nayan V.,Vail, Peter D.,Morrow, Scott D.,et al.
p. 765 - 770
(2007/10/02)
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