Intramolecularity of the thermal rearrangement of allyloxytetrazoles to n-allyltetrazolones

被引:23
作者
Cristiano, MLS [1 ]
Johnstone, RAW [1 ]
机构
[1] UNIV LIVERPOOL,DEPT CHEM,LIVERPOOL L69 3BX,MERSEYSIDE,ENGLAND
来源
JOURNAL OF CHEMICAL RESEARCH-S | 1997年 / 05期
关键词
CLAISEN REARRANGEMENT;
D O I
10.1039/a608333a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The intramolecularity of the thermal rearrangement of 1-aryl-5-allyloxy-1H-tetrazoles 1 to 1-aryl-4-allyl-1,4-dihydrotetrazol-5-ones 2 has been investigated through cross-over studies: the results support the hypothesis for a concerted sigmatropic rearrangement occurring through a highly polar transition state, in which a partially positively charged allyl group migrates from oxygen to nitrogen, without leaving the solvent cage.
引用
收藏
页码:164 / 165
页数:6
相关论文
共 17 条
[1]  
BENNETT GB, 1977, SYNTHESIS-STUTTGART, P589
[2]   THE HETERO-COPE REARRANGEMENT IN ORGANIC-SYNTHESIS [J].
BLECHERT, S .
SYNTHESIS-STUTTGART, 1989, (02) :71-82
[3]  
Bunnet J. P., 1974, TECHNIQUES CHEM 1, V6, P129
[4]  
Cristiano M. L S., 1996, J CHEM SOC P1, V1, P1453, DOI DOI 10.1039/P19960001453
[5]  
CRISTIANO MLS, 1994, THESIS U LIVERPOOL
[6]  
CRISTIANO MLS, 1996, IN PRESS J CHEM S P1
[7]   SOME CLAISEN REARRANGEMENTS IN HETEROCYCLIC SYSTEMS [J].
ELWOOD, JK ;
GATES, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (10) :2956-+
[8]   NEW SYNTHETIC METHODOLOGY FOR THE SYNTHESIS OF 7-SUBSTITUTED TETRAHYDROAZEPIN-2-ONES [J].
EVANS, PA ;
HOLMES, AB ;
RUSSELL, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23) :3397-3409
[9]   New methodology for the synthesis of unsaturated 8-, 9- and 10-membered lactams [J].
Evans, PA ;
Holmes, AB ;
McGeary, RP ;
Nadin, A ;
Russell, K ;
OHanlon, PJ ;
Pearson, ND .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (02) :123-138
[10]  
KAWER JC, 1967, J ORG CHEM, V32, P3580