Bent structure and dynamic stereochemistry of chiral acridinium cations

被引：22

作者：

Laleu, B

Herse, C

Laursen, BW

Bernardinelli, G

Lacour, J

机构：

[1] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland

[2] Nano Sci Ctr, Dept Chem, DK-2100 Copenhagen, Denmark

[3] Univ Geneva, Cristallog Lab, CH-1211 Geneva 4, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 16期

关键词：

D O I：

10.1021/jo0345998

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral acridinium cations, easily prepared by reaction of enantiopure primary amines and tris(2,6-dimethoxy)trityl cation, display restricted rotations around the C(sp(3))-N(sp(2)) bond. A bending of the aromatic backbone and "out-of-plane" displacements of C(9) and N(10) atoms are enforced if bulky amines are introduced.

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页码：6304 / 6308

页数：5

相关论文

共 26 条

[1] Preparation of (R)- and (S)-1-adamantyl-9-anthrylmethanol.: Conformational study and their behaviour as chiral solvating agents [J].

Almer, S ;

Cervelló, E ;

Jaime, C ;

Virgili, A .

TETRAHEDRON-ASYMMETRY, 1999, 10 (19) :3719-3725

[2] ISOLABLE ROTAMERS OF N-(9-FLUORENYL)-PYRIDINIUM SALTS OWING TO RESTRICTED ROTATION AROUND THE C(SP3) - N+(SP2) SINGLE BOND [J].

BALABAN, AT ;

GHEORGHIU, MD ;

BALABAN, TS .

JOURNAL OF MOLECULAR STRUCTURE, 1984, 114 (MAR) :363-366

[3] ROTATION BARRIERS IN N-SUBSTITUTED 2,4,6-TRIMETHYLPYRIDINIUM CATIONS [J].

BALABAN, AT ;

UNCUTA, C ;

DINCULESCU, A ;

ELIAN, M ;

CHIRALEU, F .

TETRAHEDRON LETTERS, 1980, 21 (16) :1553-1556

[4] HINDERED ROTATION AROUND THE N+(SP2)-C(SP3) SINGLE BOND IN 2,4,6-TRIMETHYL-N-ALKYLPYRIDINIUM CATIONS - H-1 DNMR ANALYSIS [J].

BALABAN, AT ;

UNCUTA, C ;

ELIAN, M ;

CHIRALEU, F ;

DINCULESCU, A .

TETRAHEDRON, 1984, 40 (13) :2547-2553

[5] CHIRAL ROTAMERS OF N-(1-INDANYL)-PYRIDINIUM SALTS AND THEIR RESTRICTED ROTATION AROUND THE C(SP3)-N+(SP2) SINGLE BOND [J].

BALABAN, TS ;

GHEORGHIU, MD ;

ROUSSEL, C ;

BALABAN, AT .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1985, 40 (11) :1555-1557

[6] STERIC INTERPLAY BETWEEN ALKYL-GROUPS BONDED TO PLANAR FRAMEWORKS [J].

BERG, U ;

LILJEFORS, T ;

ROUSSEL, C ;

SANDSTROM, J .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (03) :80-86

[7] Photoalkylation of 10-alkylacridinium ion via a charge-shift type of photoinduced electron transfer controlled by solvent polarity [J].

Fukuzumi, S ;

Ohkubo, K ;

Suenobu, T ;

Kato, K ;

Fujitsuka, M ;

Ito, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (35) :8459-8467

[8]

HERSE C, IN PRESS ANGEW CHEM

[9] CONFORMATIONAL STUDY OF (R)-(-)-2,2,2-TRIFLUORO-1-(9-ANTHRYL)ETHANOL (PIRKLE ALCOHOL) BY DYNAMIC NMR [J].

JAIME, C ;

VIRGILI, A ;

CLARAMUNT, RM ;

LOPEZ, C ;

ELGUERO, J .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6521-6523

[10] Conformation and stereodynamics of alkyl 9-anthryl sulfoxides [J].

Jennings, WB ;

Kochanewycz, MJ ;

Lunazzi, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (11) :2271-2273