新しい有機合成反応の開発に関する研究 : 有機硫黄, スズ, ニトロ化合物を利用する合成反応

概要

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Divalent sulfur can stabilize both of carbenium ion and carbanion adjacent to the sulfur atom, and hypervalent sulfur functions can strongly stabilize the adjacent carbanions. These sulfur functions can undergo characteristic migration and/or elimination. Single electron transfer onto an aliphatic nitro compound leads to an unstable radical-anion which eliminates the nitrite anion to leave the corresponding free radical. The subsequent reaction of the free radical gives various compounds including denitrated product. And it results a new denitro-hydrogenation reaction. Nitro group can be a good leaving group in allylic system and also for the Friedel-Crafts reaction. Using these characteristics of sulfur and nitro functions twenty-five kinds of convenient synthetic reactions are presented here. The sulfur and nitro functions can assure regio- and stereocontrol of these reactions to give the desired products in most of which no sulfur function or nitro group is remained.
社団法人有機合成化学協会の論文