ChemInform Abstract: Reaction of 1‐Phenylpyrrolidin‐2‐ones with the Vilsmeier Reagent. Novel Rearrangement of δ2‐Pyrrolines Bearing a β‐ Chlorovinylaldehyde Fragment.

Abstract

Reaction of 1-Phenylpyrrolidin-2-ones with the Vilsmeier Reagent. Novel Rearrangement of δ2-Pyrrolines Bearing a β-Chlorovinylaldehyde Fragment.-Vilsmeier-Haack formylation of arylpyrrolidinone (I) followed by alkaline work-up yields a δ2-pyrroline-3-carbaldehyde (III), which rearranges quantitatively in organic solvents already at room temp. into methylenepyrrolidinone (IV). The novel rearrangement is of obvious generality for such types of pyrrolines having various substituents in the β-position to the vinylaldehyde fragment. -(FROLOV, S. I.; NEGREBETSKII, V. V.; NURIDZHANYAN, K. A.; Zh. Org. Khim. 28 (1992) 5, 1069-1074; Vses. nauchno-issled. inst. khim. sredstv zashch. rast., USSR; RU)