61923-84-0Relevant articles and documents
Iron-Catalyzed Carbenoid-Transfer Reactions of Vinyl Sulfoxonium Ylides: An Experimental and Computational Study
Vaitla, Janakiram,Bayer, Annette,Hopmann, Kathrin H.
supporting information, p. 16180 - 16184 (2018/11/23)
A method for the generation of unprecedented vinyl carbenoids from sulfoxonium ylides has been developed and applied in the synthesis of a diverse array of heterocycles such as indolizines, pyrroles, 3-pyrrolin-2-ones, and furans. The reactions proceed by FeBr2 catalysis under mild reaction conditions with a broad substrate scope. A reaction pathway involving iron carbenoids is proposed based on a series of control experiments and DFT calculations.
New ring expansion of cyclobutanones: Synthesis of pyrrolinones, pyrrolidines and pyrroles
Verniest, Guido,Boterberg, Stefaan,Bombeke, Filip,Stevens, Christian V.,De Kimpe, Norbert
, p. 1059 - 1063 (2007/10/03)
2,2-Dichlorocyclobutanones reacted with various amines to give ring opening leading to 4,4-dichlorobutanamides. These compounds proved to be suitable substrates for the synthesis of 3-pyrrolin-2-ones, 2-pyrrolidinones, pyrrolidines and pyrroles.
Synthesis and Reactions of α-Chloro-β,γ-unsaturated Esters. 1
Mathew, Jacob,Alink, Ben
, p. 3880 - 3886 (2007/10/02)
Four new α-chloro-β,γ-unsaturated esters were prepared in good yield by the reaction of hypochlorous acid with substituted ethyl 2-butenoates.Reaction of these substituted allylic chlorides with several nucleophiles has been investigated.Thiophenol in the presence of aqueous sodium hydroxide react with ethyl 2-chloro-3-methyl-3-butenoate (2) to give 6, whereas ethyl 2-chloro-2,3-dimethyl-3-butenoate (1) is unreactive.Tertiary allylic chlorides 1, 3 and 4 react with secondary amines to give exclusive abnormal SN2 reaction products.With benzylamine abnormal SN2 substitution is followed by cyclization to give 1-benzyl-3-pyrrolin-2-ones.While ethyl lithioacetate reacts with 1 to give acylation product 18, sodium diphenylmethide in liquid ammonia undergoes alkylation on the tertiary carbon possibly by an electron-transfer reaction pathway.Lithio-1,3-dithiane reacts with 1 to give 2,3-dimethyl-6,10-dithiaspirodec-2-en-1-one (20) via a two-step process, viz., acylation followed by anovel variation of the intramolecular abnormal SN2 reaction.Raney nickel desulfurization of 20 gave 2,3-dimethyl-2-cyclopenten-1-one.Synthetic and mechanistic implications of these results are discussed.