Thallium trinitrate mediated ring contraction of monocyclic ketones: Stereochemical aspects

被引：27

作者：

Ferraz, HMC

Silva, LF

机构：

[1] Instituto de Química, Universidade de Säo Paulo

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 11期

基金：

巴西圣保罗研究基金会;

关键词：

D O I：

10.1016/S0040-4039(97)00246-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 3- and 4-alkylcyclohexanones with thallium trinitrate (TTN) leads to the alkylcyclopentanecarboxylic acids in good yields and with high degree of stereoselectivity. The ring contraction of 2-methylcyclohexanone gives poor yields and 2,6-dimethylcyclohexanone does not undergo contraction. The observed diastereoselectivities of the reactions agree with the mechanism proposed by McKillop et al. (C) 1997 Elsevier Science Ltd.

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页码：1899 / 1902

页数：4

相关论文

共 17 条

[1] ANNELATION STUDIES USING 1,4-DIBROMO AND 1,5-DIBROMO DERIVATIVES IN THE PRESENCE OF CARBANIONS [J].

CANONNE, P ;

PLAMONDON, J .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (03) :555-564

[2] CYCLIZATION OF UNSATURATED MONOTERPENIC ALCOHOLS MEDIATED BY THALLIUM-(III) SALTS [J].

FERRAZ, HMC ;

RIBEIRO, CMR ;

GRAZINI, MVA ;

BROCKSOM, TJ ;

BROCKSOM, U .

TETRAHEDRON LETTERS, 1994, 35 (10) :1497-1500

[3] THALLIUM (III) SALTS-INDUCED LACTONIZATIONS OF UNSATURATED CARBOXYLIC-ACIDS [J].

FERRAZ, HMC ;

RIBEIRO, CMR .

SYNTHETIC COMMUNICATIONS, 1992, 22 (03) :399-404

[4] THE STEREOSELECTIVE SYNTHESIS OF TERPENE TETRAHYDROFURANS USING THALLIUM TRIACETATE [J].

FERRAZ, HMC ;

BROCKSOM, TJ ;

PINTO, AC ;

ABLA, MA ;

ZOCHER, DHT .

TETRAHEDRON LETTERS, 1986, 27 (07) :811-814

[5]

GRANGER R, 1969, B SOC CHIM FR, P2806

[6]

HOBERG H, 1991, SYNTHESIS-STUTTGART, P395

[7] STEREOSPECIFIC THALLIUM (III) NITRATE MEDIATED CONVERSION OF BICYCLO[3.2.1]-2-OCTANONE TO EXO-2-NORBORNANECARBOXYLIC ACID METHYL-ESTER [J].

IRWIN, AJ ;

JONES, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (12) :2176-2177

[8] CONJUGATE ADDITION-REACTIONS OF ALPHA,BETA-UNSATURATED KETONES WITH HIGHER-ORDER, MIXED ORGANOCUPRATE REAGENTS, R2CU(CN)LI2 [J].

LIPSHUTZ, BH ;

WILHELM, RS ;

KOZLOWSKI, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :3938-3942

[9] OXIDATION OF STEROID ALPHA-DIKETONES BY THALLIUM(III) ACETATE - CRYSTAL AND MOLECULAR-STRUCTURE OF A SPIRO-CYCLOPENTAN-A,S-INDACENO DERIVATIVE OBTAINED FROM 3,4-DIKETO STEROIDS [J].

MAIONE, AM ;

ROMEO, A ;

CERRINI, S ;

FEDELI, W ;

MAZZA, F .

TETRAHEDRON, 1981, 37 (07) :1407-1413

[10] THALLIUM IN ORGANIC SYNTHESIS .35. OXIDATION OF CYCLOHEXANONES TO ADIPOINS USING THALLIUM(III) NITRATE 1 [J].

MCKILLOP, A ;

TAYLOR, EC ;

HUNT, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (21) :3381-&