REGIOSPECIFIC THERMAL REARRANGEMENTS OF 2-ALLYLOXYPYRIDINE N-OXIDES

被引:7
作者
ALKER, D [1 ]
MAGESWARAN, S [1 ]
OLLIS, WD [1 ]
SHAHRIARIZAVAREH, H [1 ]
机构
[1] UNIV SHEFFIELD,DEPT CHEM,SHEFFIELD S3 7HF,S YORKSHIRE,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 06期
关键词
D O I
10.1039/p19900001631
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The results reported of an earlier investigation of the thermal rearrangement of derivatives of 2-allyloxypyridine N-oxide have been shown to be incorrect. Only [1,4] and [3,3] sigmatropic rearrangements are observed and this regiospecificity supports the view that these [1,4] and [3,3] rearrangements proceed by concerted symmetry-allowed pathways.
引用
收藏
页码:1631 / 1635
页数:5
相关论文
共 34 条
[1]   THE SYNTHESIS OF UNUSUAL ORGANIC-MOLECULES FROM AZOALKANES [J].
ADAM, W ;
DELUCCHI, O .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (10) :762-779
[2]   PERISELECTIVITY BETWEEN THE [1,4] AND [3,3] THERMAL SIGMATROPIC REARRANGEMENTS OF 2-ALLYLOXYPYRIDINE N-OXIDES [J].
ALKER, D ;
OLLIS, WD ;
SHAHRIARIZAVAREH, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06) :1623-1630
[3]   GROUND-STATES OF MOLECULES .26. MINDO-3 CALCULATIONS FOR HYDROCARBONS [J].
BINGHAM, RC ;
DEWAR, MJS ;
LO, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1294-1301
[4]   FORMATION OF (Z,E)-1,3-DIPHENYLALLYL RADICAL FROM (Z,E)-1,3-DIPHENYLALLYL ANION BY ELECTRON-TRANSFER - COMPARISON OF ROTATIONAL BARRIERS OF RADICAL AND ANION [J].
BOCHE, G ;
SCHNEIDER, DR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (12) :869-870
[5]   GEOMETRICAL ISOMERIZATION OF ALLYLIC RADICALS [J].
CRAWFORD, RJ ;
HAMELIN, J ;
STREHLKE, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (15) :3810-&
[6]  
DOLLING UH, 1975, J CHEM SOC CHEM COMM, P545, DOI 10.1039/c39750000545
[7]   MECHANISM OF THE THERMAL AND PHOTOCHEMICAL DECOMPOSITION OF AZOALKANES [J].
ENGEL, PS .
CHEMICAL REVIEWS, 1980, 80 (02) :99-150
[8]   ANODIC SYNTHESES .15. FURTHER STUDIES WITH ETHYLENIC ACIDS [J].
GARWOOD, RF ;
DIN, NU ;
SCOTT, CJ ;
WEEDON, BCL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (22) :2714-2721
[9]   EQUILIBRIUM CONSTANT FOR ALLYL RADICAL RECOMBINATION . DIRECT MEASUREMENT OF ALLYL RESONANCE ENERGY [J].
GOLDEN, DM ;
GAC, NA ;
BENSON, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (08) :2136-&
[10]   KINETICS OF CIS-TRANS-ISOMERIZATION OF 1-METHYLALLYL RADICAL - NEW TECHNIQUE FOR STUDY OF UNIMOLECULAR RADICAL REACTIONS [J].
GORTON, PJ ;
WALSH, R .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (13) :783-&