POLAR EFFECTS IN THE TRANSITION-STATE OF THE BERGMAN CYCLIZATION

被引：62

作者：

SCHMITTEL, M

KIAU, S

机构：

来源：

CHEMISTRY LETTERS | 1995年 / 10期

关键词：

D O I：

10.1246/cl.1995.953

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

the kinetic data of enediynes 1a-c it is concluded that electron withdrawing substituents are lowering the free activation energy in the Bergman cycloaromatization by decreasing the repulsion of the in-plane pi-orbitals.

引用

页码：953 / 954

页数：2

共 12 条

[1] ADDITIVITY RULES FOR ESTIMATION OF THERMOCHEMICAL PROPERTIES [J].

BENSON, SW ;

CRUICKSHANK, FR ;

GOLDEN, DM ;

HAUGEN, GR ;

ONEAL, HE ;

RODGERS, AS ;

SHAW, R ;

WALSH, R .

CHEMICAL REVIEWS, 1969, 69 (03) :279-+

[2]

CLARK T, 1991, VAMP 4 5

[3]

DEWER MJS, 1985, J AM CHEM SOC, V107, P3902

[4] COMPARISON OF BIRADICAL FORMATION BETWEEN ENEDIYNE AND ENYNE ALLENE - ABINITIO CASSCF AND MRSDCI STUDY [J].

KOGA, N ;

MOROKUMA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :1907-1911

[5] CCSD(T) INVESTIGATION OF THE BERGMAN CYCLIZATION OF ENEDIYNE - RELATIVE STABILITY OF O-DIDEHYDROBENZENE, M-DIDEHYDROBENZENE, AND P-DIDEHYDROBENZENE [J].

KRAKA, E ;

CREMER, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (11) :4929-4936

[6] AB-INITIO STUDY OF THE BERGMAN REACTION - THE AUTOAROMATIZATION OF HEX-3-ENE-1,5-DIYNE [J].

LINDH, R ;

PERSSON, BJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (11) :4963-4969

[7]

MAIER ME, 1992, LIEBIGS ANN CHEM, P855

[8]

NICOLAOU KC, 1991, ANGEW CHEM, V103, P1453

[9] THE ENERGY WELL OF DIRADICALS .5. 1,3,5-CYCLOHEXATRIENE-1,4-DIYL AND 2,4-CYCLOHEXADIENE-1,4-DIYL [J].

ROTH, WR ;

HOPF, H ;

HORN, C .

CHEMISCHE BERICHTE, 1994, 127 (09) :1765-1779

[10] ELECTRON-TRANSFER INITIATED DIELS-ALDER REACTION WITH ALLENES AS DIENOPHILES [J].

SCHMITTEL, M ;

WOHRLE, C .

TETRAHEDRON LETTERS, 1993, 34 (52) :8431-8434

← 1 2 →