Journal of Organic Chemistry p. 765 - 770 (1981)
Update date:2022-08-02
Topics:
Wade, Peter A.
Hinney, Harry R.
Amin, Nayan V.
Vail, Peter D.
Morrow, Scott D.
et al.
(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.
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Doi:10.1021/jo00317a043
(1981)Doi:10.1016/S0040-4039(00)77411-9
(1980)Doi:10.1021/ja01175a063
(1949)Doi:10.1021/np0400353
(2004)Doi:10.1016/S0040-4039(00)77414-4
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(1981)
