The Journal of Organic Chemistry

Stereoelectronic effects in tertiary amine nitrosation: Nitrosative cleavage vs. aryl ring nitration

RN Leoppky, W Tomasik

文献索引：Leoppky, Richard N.; Tomasik, Witold Journal of Organic Chemistry, 1983 , vol. 48, # 16 p. 2751 - 2757

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被引用次数: 18

摘要

The nitrosation (acetic acid) of N-(4-chlorophenyl) pyrrolidine gives at least 30% N-(4-chloro- 2-nitropheny1) pyrrolidine while the corresponding aryldibenzylamine gives no nitration and only nitrosative dealkylation at nitrogen. Thia difference in reaction site has been probed with N-(4-~ hlorophenyl) diethylamine. This substance undergoes competitive ring nitration to N-(4-chloro-2-nitrophenyl) diethylamine (50%) and nitrosative dealkylation to (4- ...