CONFORMATIONS AND RELATIVE ENERGIES OF TETRAHYDROPYRIDINES

被引：6

作者：

BACHRACH, SM

LIU, MX

机构：

[1] Department of Chemistry Northern Illinois University DeKalb

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(00)61772-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ground state conformations of three tetrahydropyridine isomers (2,3,4,5-tetrahydropyridine 1, 1,2,3,4-tetrahydropyridine 2, and 1,2,3,6-tetrahydropyridine 3), optimized at MP2/6-31G*, are half chairs. The only conformation found for 2 has the nitrogen lone pair in the axial position in order to conjugate with the pi-bond. The relative energies of 1-3 are 0.0, 6.39, and 11.9 kcal/mol. The equatorial conformer of 3 lies 0.32 kcal/mol above the axial form.

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页码：6771 / 6774

页数：4

相关论文

共 11 条

[1]

Anet F. A. L., 1989, CONFORMATIONAL ANAL, P1

[2] CYCLIC ALLYLAMINE-ENAMINE SYSTEMS .7. A THEORETICAL-STUDY OF THE RELATIVE ENERGIES OF ISOMERIC CYCLIC ALLYLAMINE-ENAMINE SYSTEMS [J].

ASHCROFT, WR ;

CARRINGTON, NR ;

FIELD, MJ ;

HILLIER, IH ;

JOULE, JA ;

POPE, SA ;

WATT, CIF ;

GUEST, MF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (08) :1187-1190

[3]

BEEKEN P, 1980, J ORG CHEM, V45, P1336, DOI 10.1021/jo01295a043

[4]

Boger D. L., 1987, HETERO DIELS ALDER M

[5] A GENERAL-SOLUTION TO IMPLEMENTING THE 4-PI PARTICIPATION OF 1-AZA-1,3-BUTADIENES IN DIELS-ALDER REACTIONS - INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF ALPHA,BETA-UNSATURATED N-BENZENESULFONYL IMINES [J].

BOGER, DL ;

KASPER, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (04) :1517-1519

[6] ROOM-TEMPERATURE, ENDO-SPECIFIC 1-AZA-1,3-BUTADIENE DIELS-ALDER REACTIONS - ACCELERATION OF THE LUMO(DIENE)-CONTROLLED [4+2]-CYCLOADDITION REACTIONS THROUGH NONCOMPLEMENTARY AZADIENE SUBSTITUTION [J].

BOGER, DL ;

CORBETT, WL ;

WIGGINS, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :2999-3000

[7] DIELS-ALDER REACTIONS OF 1-AZA-1,3-BUTADIENES - ROOM-TEMPERATURE, ENDO-SELECTIVE LUMODIENE-CONTROLLED [4+2]-CYCLOADDITION REACTIONS OF N-SULFONYL-4-(ETHOXYCARBONYL)-1-AZA-1,3-BUTADIENES [J].

BOGER, DL ;

CURRAN, TT .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (20) :5439-5442

[8] SYNTHESIS OF THE KETODIFLUOROMETHYLENE DIPEPTIDE ISOSTERE [J].

DAMON, DB ;

HOOVER, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6439-6442

[9] STRUCTURE OF DROPERIDOL-ETHANOL (1/1) [J].

KLEIN, CL ;

WELCH, J ;

SOUTHALL, LC .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :650-653

[10] HEATS OF FORMATION OF SOME ENAMINES [J].

PROCHAZK.M ;

KRESTANO.V ;

PALECEK, M ;

PECKA, K .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1970, 35 (12) :3813-&