Reverse Cope elimination reactions. 1. Mechanism and scope

…, JM Read Jr, JC Calabrese

Index: Ciganek, Engelbert; Read, John M.; Calabrese, Joseph C. Journal of Organic Chemistry, 1995 , vol. 60, # 18 p. 5795 - 5802

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Citation Number: 72

Abstract

N-4-Pentenyl-and N-5-hexenyl-N-methylhydroxylamine cyclized under mild conditions in a reverse Cope elimination reaction to give 1, 2-dimethylpyrrolidine N-oxide and 172- dimethylpiperidine N-oxide, respectively. The reaction was shown to be concerted and thermodynamically controlled. The scope of this novel cyclization is discussed, and comparisons are made with the closely related and previously reported cyclization of ...

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