631898-76-5Relevant academic research and scientific papers
Synthesis of substituted 3-arylpiperidines and 3-arylpyrrolidines by radical 1,4 and 1,2-aryl migrations
Gheorghe, Alexandru,Quiclet-Sire, Béatrice,Vila, Xavier,Zard, Samir Z.
, p. 7187 - 7212 (2008/02/07)
A route to 3-arylpiperidines and 3-arylpyrrolidines involving radical 1,4- and 1,2-aryl migrations has been explored. For the piperidines, the first route requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with lauroyl peroxide to give the corresponding 1,4-aryl transfer product. This compound can be converted into the desired piperidine derivative following acidic hydrolysis. For the second approach to piperidines, addition of an α-keto xanthate to olefins of type 14 causes 1,2-aryl migration leading to an α,β-unsaturated ester, which can be converted into a piperidine by the action of ammonia or a primary amine and sodium cyanoborohydride. Substituted 3-arylpyrrolidines can be obtained by simply starting with an α-amido substituted xanthate.
New radical homoallylation reactions
Ouvry, Gilles,Zard, Samir Z.
, p. 1627 - 1630 (2007/10/03)
Xanthate addition to 3-aryl-4-methanesulfonylbutene and structurally related derivatives triggers a cascade involving aryl migration and elimination of a sulfonyl radical, the result being an overall homoallylation of the initial radical. Other slow migra
