A PM3 STUDY OF THE REACTIONS OF PROPENE WITH SINGLET OXYGEN AND OTHER ENOPHILES

被引：25

作者：

DAVIES, AG

SCHIESSER, CH

机构：

[1] DEAKIN UNIV,DEPT CHEM & ANALYT SCI,GEELONG,VIC 3217,AUSTRALIA

[2] UNIV LONDON UNIV COLL,DEPT CHEM,LONDON WC1H 0AJ,ENGLAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)96913-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two alternative reaction pathways, one involving a 6-membered ring transition state, the other, a strained 3-membered intermediate, have been located on the PM3 semi-empirical potential energy surfaces for the reactions of singlet oxygen, nitrosyl hydride, nitrosoformaldehyde, diazene, 1,2,4-triazoline-3,5-dione and methyleneamine with propene. Except for nitrosyl hydride, the calculations suggest that both pathways have similar energy requirements in each case.

引用

收藏

页码：1707 / 1726

页数：20

相关论文

共 46 条

[1] HOW MECHANISTICALLY EQUIVALENT ARE SINGLET OXYGEN AND TRIAZOLINEDIONE - REGIOCHEMICAL AND STEREOCHEMICAL DIFFERENCES IN THEIR ENE REACTIONS WITH ALLYLSILANES [J].

ADAM, W ;

SCHWARM, M .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) :3129-3130

[2] DIHYDROGEN TRANSFER-REACTIONS - AN SCF-MO STUDY OF THE RELATIVE ENERGIES OF THE CONCERTED AND STEPWISE PATHWAYS [J].

AGRAFIOTIS, DK ;

RZEPA, HS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (12) :902-904

[3] SINGLET OXYGEN AND TRIAZOLINEDIONE ADDITIONS TO ALPHA,BETA-UNSATURATED SULFOXIDES [J].

AKASAKA, T ;

MISAWA, Y ;

GOTO, M ;

ANDO, W .

TETRAHEDRON, 1989, 45 (21) :6657-6666

[4] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[5] REARRANGEMENT OF STRAINED DIPOLAR SPECIES, AZIRIDINE N-OXIDES .2. [J].

BALDWIN, JE ;

BHATNAGA.AK ;

CHOI, SC ;

SHORTRID.TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (16) :4082-&

[6]

Broyden C. G., 1970, Journal of the Institute of Mathematics and Its Applications, V6, P222

[7]

Burkert U., 1982, ACS MONOGRAPH

[8] REACTION OF ELECTROPHILES WITH UNSATURATED SYSTEMS - TRIAZOLINEDIONE-OLEFIN REACTIONS [J].

CHENG, CC ;

SEYMOUR, CA ;

PETTI, MA ;

GREENE, FD ;

BLOUNT, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (16) :2910-2916

[9]

Davies A. R., UNPUB

[10] FORMATION OF HYDROPEROXIDE FROM SINGLET OXYGEN AND PROPENE - A DUALITY OF MECHANISMS BY PM3 [J].

DAVIES, AG ;

SCHIESSER, CH .

TETRAHEDRON LETTERS, 1989, 30 (50) :7099-7102

← 1 2 3 4 5 →