Steric effects in high pressure Knoevenagel reactions

被引：47

作者：

Jenner, G ^{[1
]}

机构：

[1] Univ Strasbourg, Fac Chim, UMR 7509, Lab Piezochim Organ, F-67008 Strasbourg, France

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 02期

关键词：

Knoevenagel reactions; steric effects; pressure; hindered; alkenes;

D O I：

10.1016/S0040-4039(00)01930-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pressure effect in Knoevenagel condensations involving ketones and ethyl cyanoacetate is studied. The reactions are diversely affected. For cyclic ketones there is a small effect on the reaction yield. However, in the case of acyclic ketones, the sensitivity of the reaction to pressure increases with increasing steric congestion of the ketone. Such a result highlights the synthetic utility of high pressure for the preparation of hindered functionalized alkenes. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：243 / 245

页数：3

共 13 条

[1]

[Anonymous], IZV AKAD NAUK SSR KH

[2] PARAMETERS IN SIMON EQUATION RELATING PRESSURE AND MELTING TEMPERATURE [J].

BABB, SE .

REVIEWS OF MODERN PHYSICS, 1963, 35 (02) :400-&

[3] ACTIVATION VOLUME AS A MEASURE OF E2-E1CB CHARACTER IN ELIMINATION-REACTIONS [J].

BROWER, KR ;

MUHSIN, M ;

BROWER, HE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (03) :779-782

[4]

HAMANN SD, 1956, DISCUSS FARADAY SOC, P114

[5] THE PRESSURE EFFECT ON STRAINED TRANSITION-STATES - CORRELATION BETWEEN STRAIN AND VOLUME OF ACTIVATION - MECHANISTIC AND SYNTHETIC INVOLVEMENTS [J].

JENNER, G .

JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS I, 1985, 81 :2437-2460

[6] Effect of high pressure on Michael and Henry reactions between ketones and nitroalkanes [J].

Jenner, G .

NEW JOURNAL OF CHEMISTRY, 1999, 23 (05) :525-529

[7]

Jones G., 1967, ORGANICREACTIONS, V15, P204, DOI [DOI 10.1002/0471264180.OR015.02, 10.1002/0471264180.or015.02]

[8] THE APPLICATION OF LOW-VALENT TITANIUM REAGENTS IN ORGANIC-SYNTHESIS [J].

LENOIR, D .

SYNTHESIS-STUTTGART, 1989, (12) :883-897

[9]

Lenoir D, 1979, NACHR CHEM TECHN LAB, V27, P762

[10] Liquid-phase reactions at high pressures. Part I. Hydrolysis of esters, and the Knoevenagel reaction. [J].

Newitt, DM ;

Linstead, RP ;

Sapiro, RH ;

Boorman, EJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1937, :876-883

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