154139-27-2Relevant academic research and scientific papers
Indirect Electroreductive Cyclisation of N-Allylic and N-Propargylbromo Amides and o-Bromoacryloylanilides using Nickel(II) Complexes as Electron-transfer Catalysts
Ozaki, Shigeko,Matsushita, Hidenori,Ohmori, Hidenobu
, p. 2339 - 2344 (2007/10/02)
Nickel(II) complex-catalysed indirect electroreduction of N-allylic and N-propargyl-α-bromo amides and o-bromoacryloylanilides gave the corresponding 5-membered lactams.The product distribution was affected by the ability of the solvent to donate hydrogen atom.The electroreduction of N-allyl-N-(bromoacetyl)toluene-p-sulfonamide 1a in DMF and acetonitrile yielded as main product the 4-methylpyrrolidinone 2a (41percent) and the 4-(bromomethyl)pyrrolidinone 3a (33percent), respectively.On addition of 2 mol equiv. of a hydrogen-atom donor (Ph2PH) to the reaction of bromo amide 1a in acetonitrile, compound 1a provided compound 2a (58percent) as the sole cylised product.
