Newton L. Abramson

Diarryl-a-heteroarylmalonates from Cerium(IV)-promoted Reactions of Dialkyl Malonates with Heterocyclic Compounds

Thiophenes, furans and their benzo analogs undergo facile malonylation in the 2-position on reaction with dialkyl malonate radicals generated with cerium (IV) reagent

Anodic N-dearylation of 2-azetidinones

Abstract N-Methoxyphenyl-2-azetidinones are dearylated under mild conditions via anodic oxidation.

Cyclization of electrochemically generated nitrogen radicals. A novel synthesis of 11-substituted dibenzo[a,d]cycloheptenimines

Abstract A novel and convenient synthesis of 11-substituted dibenzo[a,d]cyclo-heptimines 10 via annelatlon of electrochemically generated aminium radicals derived from substituted 5-hydroxylamino-5-methyl-5H-dibenzo[a,d]cycloheptenes 14 is described. The scope and limitations of the reaction as well as the effects of reactor design, current density and electrode material on the yield of 10 and the carbocation rearrangement by-product 28 are discussed.

In situ NMR spectroscopic studies of aniline ortho acylation (“sugasawa reaction”): The nature of reaction intermediates and Lewis acid influence on yield

Abstract Ortho acylation of anilines by nitriles in the presence of BCl 3 and a second Lewis acid appear to proceed through an intermediate “supercomplex” including all four components. Yield improvements were obtained based on recognition that chloride affinity of the second Lewis acid governs supercomplex formation. Aniline protonation was found to be the cause of incomplete reaction.

Cyclization of electrochemically generated nitrogen radicals. : A novel synthesis of 11-substituted dibenzo[a,d]cycloheptenimine derivatives

Abstract A novel and convenient synthesis of 11-substituted dibenzo[a,d]cyclo-heptimines 10 via annelatlon of electrochemically generated aminium radicals derived from substituted 5-hydroxylamino-5-methyl-5H-dibenzo[a,d]cycloheptenes 14 is described. The scope and limitations of the reaction as well as the effects of reactor design, current density and electrode material on the yield of 10 and the carbocation rearrangement by-product 28 are discussed.