DEPROTONATION OF NITROALKANES BY BICYCLIC AMIDINE AND GUANIDINE BASES - EVIDENCE FOR MOLECULAR RECOGNITION WITHIN A CATALYTIC CYCLE FOR C-C BOND FORMATION

被引：57

作者：

BOYLE, PH ^{[1
]}

CONVERY, MA ^{[1
]}

DAVIS, AP ^{[1
]}

HOSKEN, GD ^{[1
]}

MURRAY, BA ^{[1
]}

机构：

[1] UNIV DUBLIN TRINITY COLL,DEPT CHEM,DUBLIN 2,IRELAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1992年 / 03期

关键词：

D O I：

10.1039/c39920000239

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Evidence from H-1 NMR spectroscopy, supported by X-ray crystallography, suggests that the bicyclic amidine and guanidine bases 2 and 3 react with nitroalkanes in non-polar organic solvents to give tightly-bound ion pairs 5; it is argued that homochiral analogues of these complexes may prove valuable as intermediates in enantioselective catalytic C-C bond-forming reactions.

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页码：239 / 242

页数：4

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共 21 条

[1] THE STRENGTH OF HETEROCYCLIC BASES [J].

ALBERT, A ;

GOLDACRE, R ;

PHILLIPS, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1948, (DEC) :2240-2249

[2] NITRATION STUDIES .18. CONVERSION OF LOWER NITROALKANES TO HIGHER MEMBERS OF SERIES [J].

BACHMAN, GB ;

MALESKI, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (18) :2810-&

[3] EQUILIBRIA INVOLVING ORGANIC-ANIONS IN DIMETHYLSULFOXIDE AND N-METHYLPYRROLIDIN-2-ONE - ACIDITIES, ION-PAIRING, AND HYDROGEN-BONDING [J].

BORDWELL, FG ;

BRANCA, JC ;

HUGHES, DL ;

OLMSTEAD, WN .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (16) :3305-3313

[4] ANION COORDINATION CHEMISTRY - POLYGUANIDINIUM SALTS AS ANION COMPLEXONES [J].

DIETRICH, B ;

FYLES, DL ;

FYLES, TM ;

LEHN, JM .

HELVETICA CHIMICA ACTA, 1979, 62 (08) :2763-2787

[5] CHIRAL RECOGNITION OF AROMATIC CARBOXYLATE ANIONS BY AN OPTICALLY-ACTIVE ABIOTIC RECEPTOR CONTAINING A RIGID GUANIDINIUM BINDING SUBUNIT [J].

ECHAVARREN, A ;

GALAN, A ;

LEHN, JM ;

DEMENDOZA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4994-4995

[6] ANION-RECEPTOR MOLECULES - SYNTHESIS OF A CHIRAL AND FUNCTIONALIZED BINDING SUBUNIT, A BICYCLIC GUANIDINIUM GROUP DERIVED FROM L-ASPARAGINE OR D-ASPARAGINE [J].

ECHAVARREN, A ;

GALAN, A ;

DEMENDOZA, J ;

SALMERON, A ;

LEHN, JM .

HELVETICA CHIMICA ACTA, 1988, 71 (04) :685-693

[7] ENANTIODIFFERENTIATION OF CARBOXYLATES BY CHIRAL BUILDING-BLOCKS FOR ABIOTIC ANION RECEPTORS [J].

GLEICH, A ;

SCHMIDTCHEN, FP ;

MIKULCIK, P ;

MULLER, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (01) :55-58

[8] METHODS OF SYNTHESES .13. 3,3,6,9,9-PENTAMETHYL-2,10-DIAZABICYCLO(4.4.0)-1-DECENE AND SOME DERIVATIVES [J].

HEINZER, F ;

SOUKUP, M ;

ESCHENMOSER, A .

HELVETICA CHIMICA ACTA, 1978, 61 (08) :2851-2874

[9] CRYSTAL-STRUCTURE OF [ALPHA-NITROBENZYLLITHIUM.ETHANOL]N - A LITHIUM NITRONATE-ETHANOL INTERACTION [J].

KLEBE, G ;

BOHN, KH ;

MARSCH, M ;

BOCHE, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :78-79

[10] STRUCTURE OF BENZAMIDINIUM PYRUVATE [J].

KRATOCHVIL, B ;

ONDRACEK, J ;

KRECHL, J ;

HASEK, J .

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1987, 43 :2182-2184