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

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

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 e...

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Veröffentlicht in:Tetrahedron 1991, Vol.47 (4), p.757-766
Hauptverfasser: Karady, Sandor, Corley, Edward G., Abramson, Newton L., Amato, Joseph S., Weinstock, Leonard M.
Format: Artikel
Sprache:eng
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Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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container_end_page 766
container_issue 4
container_start_page 757
container_title Tetrahedron
container_volume 47
creator Karady, Sandor
Corley, Edward G.
Abramson, Newton L.
Amato, Joseph S.
Weinstock, Leonard M.
description 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. The synthesis of the title compounds was achieved by cyclization of the aminium radicals generated by anodic oxidation of substituted hydroxylamines.
doi_str_mv 10.1016/S0040-4020(01)87065-4
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subjects Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
title Cyclization of electrochemically generated nitrogen radicals. : A novel synthesis of 11-substituted dibenzo[a,d]cycloheptenimine derivatives
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