NMR-STUDIES OF N-METHYL DERIVATIVES OF THE 2-AZABICYCLO [2.2.1]HEPTYL AND 2-AZABICYCLO[2.2.2]OCTYL RING-SYSTEMS - KINETIC PROTONATION IN DETERMINATION OF INVERTOMER PREFERENCES

被引：20

作者：

BELKACEMI, D ^{[1
]}

MALPASS, JR ^{[1
]}

机构：

[1] UNIV LEICESTER,DEPT CHEM,LEICESTER LE1 7RH,ENGLAND

来源：

TETRAHEDRON | 1993年 / 49卷 / 40期

关键词：

D O I：

10.1016/S0040-4020(01)91227-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compounds were studied by H-1, C-13, and N-15 NMR spectroscopy. Since inversion at nitrogen is rapid on the NMR time scale even at low temperatures, kinetic protonation was used to estimate invertomer ratios at ambient temperature. Invertomer preferences appear to be consistent with the operation of steric factors.

引用

收藏

页码：9105 / 9116

页数：12

相关论文

共 42 条

[1] NUCLEAR MAGNETIC-RESONANCE STUDIES OF RIGID BICYCLIC SYSTEMS .6. ANGULAR-DEPENDENCE OF VICINAL N-14-H-1 SPIN COUPLINGS IN BICYCLIC AMMONIUM-SALTS [J].

ANTEUNIS, MJO ;

BORREMANS, EAM ;

GELAN, J ;

MARCHAND, AP ;

ALLEN, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (13) :4050-4055

[2] N-15 NUCLEAR-MAGNETIC-RESONANCE STUDIES OF AZABICYCLES - UNUSUAL DESHIELDING OF NITROGEN IN THE 7-AZABICYCLO[2.2.1]HEPTYL RING-SYSTEM [J].

BELKACEMI, D ;

DAVIES, JW ;

MALPASS, JR ;

NAYLOR, A ;

SMITH, CR .

TETRAHEDRON, 1992, 48 (46) :10161-10176

[3]

BELKACEMI D, UNPUB

[4] A NEW ISOQUINUCLIDINE SYNTHESIS . A NEW ROUTE TO DL-DIOSCORONE [J].

CAVA, MP ;

WILKINS, CK ;

DALTON, DR ;

BESSHO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (11) :3772-&

[5] CONFORMATIONAL EFFECTS IN COMPOUNDS WITH 6-MEMBERED RINGS .12. CONFORMATIONAL EQUILIBRIUM IN N-METHYLPIPERIDINE [J].

CROWLEY, PJ ;

ROBINSON, MJT ;

WARD, MG .

TETRAHEDRON, 1977, 33 (09) :915-925

[6] FORMAL DYOTROPIC REARRANGEMENTS OF N-CHLOROAMINES CATALYZED BY ALUMINA [J].

DAVIES, JW ;

MALPASS, JR ;

WALKER, MP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (11) :686-687

[7] ELECTRONIC CONTROL OF STEREOSELECTIVITY IN THE CHLORINATION OF 1,4-DIHYDRO-1,4-IMINONAPHTHALENES (7-AZABENZONORBORNADIENES) WITH N-CHLOROSUCCINIMIDE [J].

DAVIES, JW ;

DURRANT, ML ;

WALKER, MP ;

MALPASS, JR .

TETRAHEDRON, 1992, 48 (21) :4379-4398

[8] PREPARATION AND SPECTROSCOPIC STUDIES OF THE 1,4-DIHYDRO-1,4-IMINONAPHTHALENE (7-AZABENZONORBORNADIENE) RING-SYSTEM [J].

DAVIES, JW ;

DURRANT, ML ;

WALKER, MP ;

BELKACEMI, D ;

MALPASS, JR .

TETRAHEDRON, 1992, 48 (05) :861-884

[9] UNUSUAL DESHIELDING OF N-15 IN BICYCLIC AMINES AND HYDRAZINES [J].

DAVIES, JW ;

MALPASS, JR .

TETRAHEDRON LETTERS, 1985, 26 (37) :4537-4538

[10] ORGANIC STRUCTURE CHARACTERIZATION BY NATURAL-ABUNDANCE N-15 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY - RAUWOLFIA ALKALOIDS AND MODEL COMPOUNDS [J].

FANSOFREE, SNY ;

FURST, GT ;

SRINIVASAN, PR ;

LICHTER, RL ;

NELSON, RB ;

PANETTA, JA ;

GRIBBLE, GW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (06) :1549-1553

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