Acetylenes as potential antarafacial components in concerted reactions. Formation of pyrroles from thermolyses of propargyl amines, of a dihydrofuran from a …

…, JJ Collins, N Filipp, JS Locke

文献索引：Viola, Alfred; Collins, John J.; Filipp, Nicholas; Locke, John S. Journal of Organic Chemistry, 1993 , vol. 58, # 19 p. 5067 - 5075

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被引用次数: 16

摘要

A thermal cyclization of acetylenic compounds provides evidence for the ability of acetylenic links to act as antarafacial components in [2+ 21 processes. The cyclization competes with the normally favored acetylenic retro-ene reaction. Propargylic amines, without substituents whose presence would hinder a tight cyclic transition state, yield intermediate pyrrolines whose subsequent hydrogen elimination affords pyrroles in small amounts. The same ...

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