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Functional rearrangement of 3-Cl or 3,3-diCl-gamma-lactams bearing a secondary 1-chloroalkyl substituent at C-4

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JournalTetrahedron
DatePublished - 6 Feb 2010
Issue number6
Volume66
Number of pages8
Pages (from-to)1357-1364
Original languageEnglish

Abstract

The study of the reaction with MeONa/MeOH of chlorinated gamma-lactams. prepared from the atom transfer radical cyclization of N-allyl-alpha-perchloroamides, has been extended to the case of substiates carrying an exo halogen atom on a branched carbon Only with secondary exo C-Cl groups, that are not located on a fused ring, does the functional rearrangement follow the typical transformation route, Which With trichloro-lactams can proceed further to give 4-alkylidene derivatives From a practical point of view, the outcome of the reaction with di- or trichloio N-cinnamylamides is synthetically valuable, affording the 5-methoxy-IH-pyrrol-2(5H)-one or 3-benzylidenepyrrlidine-2.5-dione. respectively. in good to excellent yield (C) 2009 Elsevier Ltd All rights reserved

    Research areas

  • Halocompound, Radical reactions, gamma-Lactams, Eluminations, Rearrangements, TRANSFER RADICAL CYCLIZATIONS, ATOM-TRANSFER CYCLIZATION, RUTHENIUM-CATALYZED CYCLIZATION, CHAETOMELLIC ANHYDRIDE-A, BOND-FORMING REACTIONS, FORMAL TOTAL SYNTHESIS, GAMMA-LACTAMS, N-ALLYLTRICHLOROACETAMIDES, STEREOSELECTIVE PREPARATION, ATRC REACTIONS

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