. alpha.-Nitro sulfones. 2. Convenient new synthesis and selected functional group transformations

PA Wade, HR Hinney, NV Amin, PD Vail…

Index: Wade, Peter A.; Hinney, Harry R.; Amin, Nayan V.; Vail, Peter D.; Morrow, Scott D.; et al. Journal of Organic Chemistry, 1981 , vol. 46, p. 765 - 770

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Citation Number: 50

Abstract

(Phenylsulfony1) nitromethane (1) is preferentially C-alkylated by benzylic halides and primary alkyl iodides, affording secondary a-nitro sulfone products. a-Nitro sulfonB are also obtained from the corresponding C-alkylation of allylic acetates in the presence of catalytic tetrakis (tripheny1phosphine) palladium. The palladium (0)-catalyzed reaction is stereospecific for geranyl and neryl acetates and is also regioeelective. Desulfonation of a ...