13618-88-7Relevant academic research and scientific papers
Radical cycloaddition by nickel(II) complex-catalyzed electroreduction. A method for preparation of pyrrolopyridine and pyrrolopyrrole derivatives
Ozaki, Shigeko,Mitoh, Shizue,Ohmori, Hidenobu
, p. 2020 - 2024 (1996)
Cycloalkano[a]pyrroles were obtained by reductive radical cycloaddition of 1-(2-iodoethyl)pyrrole and activated olefins or by cyclization of 1-(ω- iodoalkyl)pyrroles, through electroreduction of the iodides using nickel(II) complex as an electron-transfer catalyst.
Acetylenes as Potential Antarafacial Components in Concerted Reactions. Formation of Pyrroles from Thermolyses of Propargylamines, of a Dihydrofuran from a Propargylic Ether, and of an Ethylidenepyrrolidine from a β-Amino Acetylene
Viola, Alfred,Collins, John J.,Filipp, Nicholas,Locke, John S.
, p. 5067 - 5075 (2007/10/02)
A thermal cyclization of acetylenic compounds provides evidence for the ability of acetylenic links to act as antarafacial components in 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-oxabicyclooctane 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 s + 2a + 2s + 2s> Moebius process, wherein the acetylenic unit is the antarafacial component.Evidence for concertedness in these reactions is discussed.
