Stereochemistry of nucleophilic addition reactions. 5. Formation of stabilized ylides from methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-.BETA.-D-erythro-hex-2-enopyranoside with some S-ylides; an important role of the nitro group for stabilization of the
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Treatment of methyl 4,6-<I>O</I>-benzylidene-2,3-dideoxy-3-nitro-β-D-<I>erythro</I>-hex-2-enopyranoside (<B>1</B>) with dimethyloxosulfonium methylide and dimethylsulfonium α-methylphenacylide afforded cyclopropane derivatives, whereas similar reactions with dimethylsulfonium phenacylide and dimethylsulfonium ethoxycarbonylmethylide gave stabilized ylides. In all cases the <I>S</I>-ylides enter the C-2 position of <B>1</B> from the side trans to the anomeric methoxyl group. The ylide structures were determined from IR and NMR data and confirmed by transformation into the desulfurized products. Anomalous stability of these ylides are attributed to the delocalization of the negative as well as positive charge over the carbonyl and the nitro group, respectively.
- 公益社団法人 日本化学会の論文
著者
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Nakagawa Toshio
Department Of Business Administration Aichi Institute Of Technology
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Sakakibara Tohru
Department Of Chemistry Yokohama City University
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Nakagawa Toshio
Department of Chemistry, Yokohama City University
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Sudoh Rokuro
Department of Chemistry, Faculty of Science, Tokyo Institute of Technology
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