RING EXPANSION AND REARRANGEMENT REACTIONS OF N-HETEROARYLMETHYL RADICALS

被引：4

作者：

MCLELLAN, JF ^{[1
]}

MCNAB, H ^{[1
]}

MUIR, TW ^{[1
]}

机构：

[1] UNIV EDINBURGH,DEPT CHEM,W MAINS RD,EDINBURGH EH9 3JJ,MIDLOTHIAN,SCOTLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 10期

关键词：

D O I：

10.1039/c39930000839

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Flash vacuum pyrolysis of N-(p-chlorophenoxymethyl)azoles (e.g. 2 and 3) gives ring expanded products (e.g. 4 and 8) formed via N-heteroarylmethyl radicals (e.g. 1 and 6); the mechanism of ring expansion generally involves a novel 'walk'-rearrangement of the radical centre.

引用

页码：839 / 840

页数：2

共 50 条

[1] Ring opening versus ring expansion in rearrangement of bicyclic cyclobutylcarbinyl radicals
Shi, Jing
Chong, Sha-Sha
Fu, Yao
Guo, Qing-Xiang
Liu, Lei
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (03): : 974 - 982
[2] Rearrangement Reactions of Tritylcarbenes: Surprising Ring Expansion and Computational Investigation
Banert, Klaus
Hagedorn, Manfred
Pester, Tom
Siebert, Nicole
Staude, Cornelius
Tchernook, Ivan
Rathmann, Katharina
Holloczki, Oldamur
Friedrich, Joachim
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (42) : 14911 - 14923
[3] Ring expansion reactions via endocyclic cleavage of cyclopropylcarbinyl radicals
Lee, PH
Lee, B
Lee, J
Park, SK
TETRAHEDRON LETTERS, 1999, 40 (17) : 3427 - 3430
[4] FRAGMENTATION OF ALKOXY RADICALS - SYNTHESIS OF MACROLACTONES BY SEQUENTIAL RING EXPANSION REACTIONS
ARENCIBIA, T
SALAZAR, JA
SUAREZ, E
TETRAHEDRON LETTERS, 1994, 35 (40) : 7463 - 7466
[5] Free radical ring expansion and subsequent reactions of intermediary carbon radicals
Matović, Radomir
Čeković, Živorad
1996, Serbian Chemical Society (61)
[6] Cascade rearrangement of spiroepoxymethyl radicals into 2-oxocycloalkyl radicals: evaluation of a two-carbon cycloalkanone ring expansion
Afzal, M
Walton, JC
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (05): : 937 - 945
[7] Free radical-mediated ring expansion reactions: Endocyclic cleavage of cyclopropylcarbinyl radicals
Lee, PH
Lee, B
Lee, K
Lee, CH
Chang, S
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2000, 21 (06) : 595 - 603
[8] REACTIONS OF ARYLCYCLOHEXADIENYL RADICALS - REARRANGEMENT VERSUS FRAGMENTATION
ATKINSON, DJ
PERKINS, MJ
WARD, P
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (19): : 3240 - &
[9] RING EXPANSION BY SILOXY-COPE REARRANGEMENT
THIES, RW
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (06): : 237 - &
[10] ASYMMETRIC INDUCTION AND RING EXPANSION REACTIONS IN THE CHARGE PROMOTED 3-AZA-COPE REARRANGEMENT
COOK, GR
STILLE, JR
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 204 : 392 - ORGN

← 1 2 3 4 5 →