ROLE OF THE ISOMERIZATION PATHWAYS IN THE STAUDINGER REACTION - A THEORETICAL-STUDY ON THE INTERACTION BETWEEN ACTIVATED KETENES AND IMIDATES

被引:30
作者
ARRIETA, A
UGALDE, JM
COSSIO, FP
LECEA, B
机构
[1] EUSKAL HERRIKO UNIBERTSITATEA,FAK KIM,E-20080 SAN SEBASTIAN DON,SPAIN
[2] EUSKAL HERRIKO UNIBERTSITATEA,FAK FARM,E-01007 VITORIA,SPAIN
关键词
D O I
10.1016/S0040-4039(00)73385-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Theoretical studies on the Staudinger reaction between methoxyketene and a simple imidate provide an explanation for the trans stereoselectivity observed. The key step responsible for this unusual outcome is the facile interconversion between two zwitterionic intermediates through a biradical transition state.
引用
收藏
页码:4465 / 4468
页数:4
相关论文
共 20 条
[1]  
BOSE AK, 1972, TETRAHEDRON LETT, P4091
[2]   STUDIES ON LACTAMS .V. 3-AZIDO-2-AZETIDINONES [J].
BOSE, AK ;
ANJANEYU.B ;
BHATTACH.SK ;
MANHAS, MS .
TETRAHEDRON, 1967, 23 (12) :4769-&
[3]   CHIRAL CONTROL OF THE STAUDINGER REACTION [J].
COOPER, RDG ;
DAUGHERTY, BW ;
BOYD, DB .
PURE AND APPLIED CHEMISTRY, 1987, 59 (03) :485-492
[4]   A SEMIEMPIRICAL THEORETICAL-STUDY ON THE FORMATION OF BETA-LACTAMS FROM KETENES AND IMINES [J].
COSSIO, FP ;
UGALDE, JM ;
LOPEZ, X ;
LECEA, B ;
PALOMO, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :995-1004
[5]   CHIRAL CONTROL IN THE STAUDINGER REACTION BETWEEN KETENES AND IMINES - A THEORETICAL SCF-MO STUDY ON ASYMMETRIC TORQUOSELECTIVITY [J].
COSSIO, FP ;
ARRIETA, A ;
LECEA, B ;
UGALDE, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :2085-2093
[6]   MECHANISM OF THE DIELS-ALDER REACTION - REACTIONS OF BUTADIENE WITH ETHYLENE AND CYANOETHYLENES [J].
DEWAR, MJS ;
OLIVELLA, S ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :5771-5779
[7]   THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].
DEWAR, MJS ;
ZOEBISCH, EG ;
HEALY, EF ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909
[8]   MECHANISM OF THE COPE REARRANGEMENT [J].
DEWAR, MJS ;
JIE, CX .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (20) :5893-5900
[9]  
Georg GI, 1993, ORGANIC CHEM BETA LA, P295
[10]  
Ghosez L., 1991, COMPREHENSIVE ORGANI, V5, P85