The vinylcyclopropane-cyclopentene rearrangement: A prototype thermal rearrangement involving competing diradical concerted and stepwise mechanisms

被引:103
作者
Houk, KN [1 ]
Nendel, M [1 ]
Wiest, O [1 ]
Storer, JW [1 ]
机构
[1] UNIV NOTRE DAME, DEPT CHEM & BIOCHEM, NOTRE DAME, IN 46556 USA
关键词
D O I
10.1021/ja971315q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
[No abstract available]
引用
收藏
页码:10545 / 10546
页数:2
相关论文
共 27 条
[1]   STEREOCHEMISTRY OF THE THERMAL-ISOMERIZATION OF VINYLCYCLOPROPANE TO CYCLOPENTENE [J].
BALDWIN, JE ;
VILLARICA, KA ;
FREEDBERG, DI ;
ANET, FAL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10845-10846
[2]  
BALDWIN JE, 1994, TETRAHEDRON LETT, V35, P7905, DOI 10.1016/S0040-4039(00)78381-X
[3]   Stereochemistry of the thermal isomerizations of trans-1-ethenyl-2-phenylcyclopropane to 4-phenylcyclopentene [J].
Baldwin, JE ;
Bonacorsi, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (35) :8258-8265
[4]   KINETICS OF IODINE 2-CATALYZED POSITIONAL ISOMERISM OF BUTENE-1 - RESONANCE ENERGY OF ALLYL RADICAL [J].
BENSON, SW ;
NANGIA, P ;
BOSE, AN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (10) :1388-&
[5]   AB-INITIO MC-SCF STUDY OF THERMAL AND PHOTOCHEMICAL [2+2] CYCLOADDITIONS [J].
BERNARDI, F ;
BOTTONI, A ;
OLIVUCCI, M ;
VENTURINI, A ;
ROBB, MA .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1994, 90 (12) :1617-1630
[6]   CALCULATION OF EQUILIBRIUM CONSTANTS FOR ISOTOPIC EXCHANGE REACTIONS [J].
BIGELEISEN, J ;
MAYER, MG .
JOURNAL OF CHEMICAL PHYSICS, 1947, 15 (05) :261-267
[7]   Bimodal distribution of lifetimes for an intermediate from a quasiclassical dynamics simulation [J].
Carpenter, BK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (42) :10329-10330
[8]  
CHICKOS J, 1984, 187 M AM CHEM SOC
[9]   CONTINUOUS DIRADICAL AS TRANSITION-STATE - INTERNAL ROTATIONAL PREFERENCE IN THERMAL ENANTISOMERIZATION AND DIASTEREOISOMERIZATION OF CIS- AND TRANS-1-CYANO-2-ISOPROPENYLCYCLOPROPANE [J].
DOERING, WVE ;
SACHDEV, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) :1168-1187
[10]   Electronic control of stereoselectivities of electrocyclic reactions of cyclobutenes: A triumph of theory in the prediction of organic reactions [J].
Dolbier, WR ;
Koroniak, H ;
Houk, KN ;
Sheu, CM .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (10) :471-477