Not quite the last word on the Perkin reaction

被引:10
作者
Edwards, Mark [1 ]
Rourk, Paul M. [4 ]
Riby, Philip G. [2 ]
Mendham, Andrew P. [3 ]
机构
[1] Univ Greenwich, Sch Sci, Chatham ME4 4TB, Kent, England
[2] Liverpool John Moores Univ, Liverpool L3 3AF, Merseyside, England
[3] Univ Greenwich, Fac Sci & Engn, Chatham ME4 4TB, Kent, England
[4] Univ Greenwich, Sch Chem & Life Sci, London SE18 6PF, England
关键词
Perkin reaction; Microwave; Water; PFA vessels; Mechanism proposal; MICROWAVE-ENERGY;
D O I
10.1016/j.tet.2014.07.053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Microwave irradiation does not accelerate the rate of the Perkin reaction carried out under normal atmospheric pressure. Water is an essential yet catalytic reactant for the Perkin reaction to occur. Containment of the Perkin reaction in a sealed vessel improves the yield. Two pressure increases are observed during a 4 h reaction time. An induction period is seen in the Perkin reaction when sodium acetate is used as a base. A re-appraisal of the reaction mechanism is proposed on the basis of these observations. The use of PFA (R) reaction vessels enables the Perkin reaction to occur under aqueous conditions for around 80 reactions/vessel. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7245 / 7252
页数:8
相关论文
共 20 条
[1]   APPLICATION OF MICROWAVE-ENERGY TO ORGANIC-SYNTHESIS - IMPROVED TECHNOLOGY [J].
ABRAMOVITCH, RA ;
ABRAMOVITCH, DA ;
IYANAR, K ;
TAMARESELVY, K .
TETRAHEDRON LETTERS, 1991, 32 (39) :5251-5254
[2]  
Bock F., 1934, MONATSH CHEM, V64, P401
[3]  
Chappell F. L., 1933, THESIS CORNELL U
[4]   THE RAPID SYNTHESIS OF ORGANIC-COMPOUNDS IN MICROWAVE-OVENS .2. [J].
GEDYE, RN ;
RANK, W ;
WESTAWAY, KC .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1991, 69 (04) :706-711
[5]  
Johnson J. R., 1942, ORG REACTIONS, V1, P218
[6]  
Kaldin H., 1982, PROFILES DRUG SUBSTA, V11, P114
[7]   On the theory of Perkin synthesis - The mechanism of the reaction [J].
Kalnin, P .
HELVETICA CHIMICA ACTA, 1928, 11 :977-1003
[8]  
KINASTOWSKI S, 1978, B ACAD POL SCI-CHIM, V26, P907
[9]  
Kingston H.M., 1988, ACS Professional Reference Book
[10]   MICROWAVE-ENERGY FOR ACID DECOMPOSITION AT ELEVATED-TEMPERATURES AND PRESSURES USING BIOLOGICAL AND BOTANICAL SAMPLES [J].
KINGSTON, HM ;
JASSIE, LB .
ANALYTICAL CHEMISTRY, 1986, 58 (12) :2534-2541