C-13 NMR-STUDIES OF DIANIONS OF UNSATURATED CARBOXYLIC-ACIDS

被引：16

作者：

AURELL, MJ

GIL, S

MESTRES, R

PARRA, M

TORTAJADA, A

机构：

[1] Departament de Química Orgànica, Universitat de València, Burjassot, València

来源：

TETRAHEDRON | 1994年 / 50卷 / 17期

关键词：

D O I：

10.1016/S0040-4020(01)90421-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-13 NMR Spectra of the dianions Li-2-n resulting from double deprotonation of unsaturated carboxylic acids 1 to 6 by lithium dialkylamides, are examined. Higher field resonance for C-2 than for C-4 atoms are observed, which reveal higher electron density at C-2 than at C-4, in agreement with the kinetic alpha-regioselectivity exhibited by these dianions on reaction with electrophiles.

引用

页码：5109 / 5118

页数：10

共 36 条

[1] GEOMETRIC ISOMERISM IN SUBSTITUTED 4-PICOLYL CARBANIONS - A PROBE FOR RANKING THE CHARGE DEMANDS OF ELECTRON-WITHDRAWING GROUPS
ABBOTTO, A
BRADAMANTE, S
PAGANI, GA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) : 444 - 448
[2] CHARGE MAPPING IN CARBANIONS - WEAK CHARGE DEMAND OF THE CYANO GROUP AS ASSESSED FROM A C-13 NMR-STUDY OF CARBANIONS OF ALPHA-ACTIVATED ACETONITRILES AND PHENYLACETONITRILES - BREAKDOWN OF A MYTH
ABBOTTO, A
BRADAMANTE, S
PAGANI, GA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) : 449 - 455
[3] TRIENEDIOLATES OF HEXADIENOIC ACIDS IN SYNTHESIS - SYNTHESIS OF RETINOIC AND NOR-RETINOIC ACIDS
AURELL, MJ
CARNE, I
CLAR, JE
GIL, S
MESTRES, R
PARRA, M
TORTAJADA, A
[J]. TETRAHEDRON, 1993, 49 (27) : 6089 - 6100
[4] DIENEDIOLATES OF UNSATURATED CARBOXYLIC-ACIDS IN SYNTHESIS - TANDEM MICHAEL DIECKMANN SYNTHESIS OF SUBSTITUTED 2-CYCLOHEXENONES
AURELL, MJ
GAVINA, P
GIL, S
PARRA, M
TORTAJADA, A
MESTRES, R
[J]. SYNTHETIC COMMUNICATIONS, 1991, 21 (18-19) : 1825 - 1831
[5] POLYENOLATES OF UNSATURATED CARBOXYLIC-ACIDS IN SYNTHESIS - SYNTHESIS OF UNSATURATED ALPHA-AMINO-ACIDS AND GAMMA-HYDRAZINO ACIDS
AURELL, MJ
GIL, S
MARTINEZ, PV
PARRA, M
TORTAJADA, A
MESTRES, R
[J]. SYNTHETIC COMMUNICATIONS, 1991, 21 (18-19) : 1833 - 1839
[6] AURELL MJ, 1990, THESIS U VALENCIA
[7] DIENEDIOLATES FROM UNSATURATED CARBOXYLIC-ACIDS - MICHAEL ADDITION OF DILITHIUM BUTA-1,3-DIENE-1,1-DIOLATE (FROM CROTONIC ACID) TO UNSATURATED-KETONES
BALLESTER, P
COSTA, A
RASO, AG
GOMEZSOLIVELLAS, A
MESTRES, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07): : 1711 - 1717
[8] UNSATURATED CARBOXYLIC-ACID DIENOLATES - ADDITION TO SUBSTITUTED CYCLOHEXANONES - INVERTED KINETIC AND THERMODYNAMIC STEREOSELECTIVITIES
BALLESTER, P
COSTA, A
GARCIARASO, A
MESTRES, R
[J]. TETRAHEDRON LETTERS, 1987, 28 (33) : 3853 - 3856
[9] UNSATURATED CARBOXYLIC-ACID DIENOLATES - REACTION WITH SUBSTITUTED CYCLOHEXANONES AND UNSUBSTITUTED CYCLOALKANONES - REGIO-SELECTIVITY AND STEREO-SELECTIVITY
BALLESTER, P
COSTA, A
GARCIARASO, A
MESTRES, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01): : 21 - 32
[10] BALLESTER P, 1985, SYNTHESIS-STUTTGART, P802

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