Journal of Organic Chemistry p. 5067 - 5075 (1993)
Update date:2022-07-29
Topics:
Viola, Alfred
Collins, John J.
Filipp, Nicholas
Locke, John S.
A thermal cyclization of acetylenic compounds provides evidence for the ability of acetylenic links to act as antarafacial components in <2 + 2> 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 process in 2-ethynyltetrahydropyran affords 8-oxabicyclo<3.2.1>octane in 35percent yield.A related thermal reaction of N-methyl-3-hexyn-1-amine provides a quantitative transformation to N-methyl-2-ethylidenepyrrolidine in a nominal <2s + 2a + 2s + 2s> Moebius process, wherein the acetylenic unit is the antarafacial component.Evidence for concertedness in these reactions is discussed.
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