日本化学会誌
Print ISSN : 0369-4577
シドノン化合物のニトロ化 ―シドノニル基の電子効果における二元性―
田 憲儒野中 勉淵上 寿雄関根 太郎大田 正樹
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1978 巻 (1978) 9 号 p. 1310-1312

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Several new nitro derivatives of sydnone compounds were synthesized by nitration of the sydnones with potassium nitrate in concentrated sulfuric acid.3-Benzylsydnone gave 3-(mnitrobenzyl)sydonone and 3- (m-nitrobenzy1)-4-nitrosydnone on treatment with 1-2 and 6 eq. moles of the nitrating agent, respectively. The nitration of 3, 4-diphenylsydnone occurred only at the p-position of the 4-phenyl ring. From these results (summarized in Table 1), the 3- and 4-sydnonyl groups are suggested to be electron-attractive and electron-releasing, respectively, showing a duality in electronic effect of the sydnone ring.

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