Quantitating the effect of an ortho substituent on cyclization and intramolecular hydrogen-transfer reactions of aryl radicals

被引：15

作者：

Curran, DP ^{[1
]}

Fairweather, N ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 07期

关键词：

D O I：

10.1021/jo0268759

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reduction of allyl 2-iodobenzyl malonates with triphenyltin hydrides generates aryl radicals that partition between 6-exo cyclization, 7-endo cyclization, and 1,5-hydrogen atom transfer. Rate constants for all of these processes are high (> 10(8) M-1 s(-1)), and the rates are only marginally reduced (< 33%) by the introduction of methyl group ortho to the reacting radical.

引用

页码：2972 / 2974

页数：3

共 50 条

[21] Proton transfer reactions of N-aryl triazolium salts: unusual ortho-substituent effects
Tucker, David E.
Quinn, Peter
Massey, Richard S.
Collett, Christopher J.
Jasiewicz, David J.
Bramley, Christopher R.
Smith, Andrew D.
O'Donoghue, AnnMarie C.
[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2015, 28 (02) : 108 - 115
[22] On the intramolecular migrations of hydrogen and radicals in organic reactions
Silov, EA
[J]. COMPTES RENDUS DE L ACADEMIE DES SCIENCES DE L URSS, 1941, 30 : 221 - 224
[23] SANDMEYER REACTIONS .2. ESTIMATION OF ABSOLUTE RATE CONSTANTS FOR SOME HYDROGEN-TRANSFER REACTIONS AND FOR THE TRANSFER OF WATER LIGANDS ON CU-II TO ARYL RADICALS BY USE OF A PSCHORR RADICAL CLOCK
HANSON, P
HAMMOND, RC
GOODACRE, PR
PURCELL, J
TIMMS, AW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (04): : 691 - 696
[24] STEREOSELECTIVE HYDROGEN-TRANSFER REACTIONS INVOLVING ACYCLIC RADICALS - A STUDY OF RADICAL CONFORMATIONS USING SEMIEMPIRICAL CALCULATIONS
DURKIN, K
LIOTTA, D
RANCOURT, J
LAVALLEE, JF
BOISVERT, L
GUINDON, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) : 4912 - 4914
[25] HYDROGEN-TRANSFER IN CATALYTIC REACTIONS, ACCOMPANIED BY CAPILLARY CONDENSATION
OSTROVSKII, NM
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 208 : 81 - PETR
[26] Diastereoselective Hydrogen-Transfer Reactions: An Experimental and DFT Study
Godin, Francois
Prevost, Michel
Gorelsky, Serge I.
Mochirian, Philippe
Maud Nguyen
Viens, Frederick
Guindon, Yvan
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (28) : 9308 - 9318
[27] HYDROGEN-TRANSFER REACTIONS IN THE THERMAL-CRACKING OF ASPHALTENES
BEHAR, F
PELET, R
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 193 : 22 - GEOC
[28] HYDROGEN-TRANSFER REACTIONS IN THE THERMAL-CRACKING OF ASPHALTENES
BEHAR, F
PELET, R
[J]. ENERGY & FUELS, 1988, 2 (03) : 259 - 264
[29] Ortho effect in the Bergman cyclization:: Interception of p-benzyne intermediate by intramolecular hydrogen abstraction
Zeidan, TA
Manoharan, M
Alabugin, IV
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03): : 954 - 961
[30] INTRAMOLECULAR REACTIONS OF ORTHO-ALKOXY-BENZYL AND ORTHO-ALKYLTHIO-BENZYL RADICALS
CADOGAN, JIG
HUSBAND, JB
MCNAB, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (05): : 697 - 701

← 1 2 3 4 5 →