CYCLIZATION OF ELECTROCHEMICALLY GENERATED NITROGEN RADICALS - A NOVEL SYNTHESIS OF 11-SUBSTITUTED DIBENZO[A,D]CYCLOHEPTENIMINE DERIVATIVES

被引:13
作者
KARADY, S
CORLEY, EG
ABRAMSON, NL
AMATO, JS
WEINSTOCK, LM
机构
[1] Merck Sharp and Dohme Research Laboratories Process Research Department, Rahway, NJ 07065
关键词
D O I
10.1016/S0040-4020(01)87065-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and convenient synthesis of 11-substituted dibenzo[a,d]cycloheptimines 10 via annelation 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.
引用
收藏
页码:757 / 766
页数:10
相关论文
共 20 条
[1]  
[Anonymous], [No title captured]
[2]  
BRITCHER SF, 1988, Patent No. 264183
[3]   TRANS-ANNULAR REACTIONS OF DIBENZO[A,D]CYCLOALKENES .1. SYNTHESIS OF DIBENZO[A,D]CYCLOOCTEN-6,12-IMINES AND "DIBENZO[A,D]CYCLOHEPTEN-5,10-IMINES [J].
CHRISTY, ME ;
ANDERSON, PS ;
BRITCHER, SF ;
COLTON, CD ;
EVANS, BE ;
REMY, DC ;
ENGELHARDT, EL .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (18) :3117-3127
[4]  
CIGANEK E, IN PRESS J ORG CHEM
[5]   THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1. [J].
CURRAN, DP .
SYNTHESIS-STUTTGART, 1988, (06) :417-439
[6]  
Giese B., 1986, RADICALS ORGANIC SYN
[7]  
GILCHRIST TL, 1979, COMPREHENSIVE ORGANI, V2, P273
[8]   CYCLIZATION OF UNSATURATED HYDROXYLAMINE DERIVATIVES [J].
HOUSE, HO ;
MANNING, DT ;
MELILLO, DG ;
LEE, LF ;
HAYNES, OR ;
WILKES, BE .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (05) :855-863
[9]   NEW SYNTHESIS OF 2-ALKYLPYRROLIDINES AND 2-ALKYLPIPERIDINES [J].
HOUSE, HO ;
LEE, LF .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (05) :863-869
[10]   CYCLIZATION OF ELECTROCHEMICALLY GENERATED NITROGEN RADICALS - A NOVEL SYNTHESIS OF 11-SUBSTITUTED DIBENZO[A,D]CYCLOHEPTENIMINES [J].
KARADY, S ;
CORLEY, EG ;
ABRAMSON, NL ;
WEINSTOCK, LM .
TETRAHEDRON LETTERS, 1989, 30 (17) :2191-2194