PHOSPHONIC SYSTEMS .5. PROTOTROPIC EQUILIBRIA OF DIETHYL ALKENYLPHOSPHONATES

被引:18
作者
GERBER, JP [1 ]
MODRO, TA [1 ]
WAGENER, CCP [1 ]
ZWIERZAK, A [1 ]
机构
[1] UNIV PRETORIA,DEPT CHEM,PRETORIA 0002,SOUTH AFRICA
关键词
D O I
10.1002/hc.520020606
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Base-catalyzed prototropic equilibria for nine pairs of diethyl 1- and 2-alkenylphosphonates have been determined. The results, together with those reported elsewhere for three other pairs, demonstrated that the diethoxyphosphoryl group PO3Et2 has only a very weakly stabilizing effect on the adjacent carbon-carbon double bond. The decisive factors are the number of carbon atoms attached to the double bond and the number of hydrogen atoms available for hyperconjugation.
引用
收藏
页码:643 / 649
页数:7
相关论文
共 19 条
[1]  
ABRAMOV VS, 1952, ZH OBSHCH KHIM+, V22, P647
[2]   STRUCTURAL EFFECTS ON RATES AND EQUILIBRIA - EQUILIBRATION OF 5-METHYL-3-HEXEN-2-ONE AND 5-METHYL-4-HEXEN-2-ONE AND OF XCH2CH=CYZ XCH=CHCHYZ PAIRS IN GENERAL [J].
HINE, J ;
LINDEN, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (04) :584-587
[3]   STRUCTURAL EFFECTS ON RATES AND EQUILIBRIA .26. EFFECTS OF 57 SUBSTITUENTS ON THE STABILITIES OF CARBON CARBON DOUBLE-BONDS [J].
HINE, J ;
SKOGLUND, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) :4766-4770
[4]  
HINE J, 1975, STRUCTURAL EFFECTS E, pCH8
[6]   THE PROTOTROPIC EQUILIBRIA IN PENTENYLPHOSPHONIC SYSTEMS [J].
MODRO, AM ;
MODRO, TA .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (07) :1541-1545
[7]   DEALKYLATION REACTION OF ACETALS, PHOSPHONATE, AND PHOSPHATE-ESTERS WITH CHLOROTRIMETHYLSILANE-METAL HALIDE REAGENT IN ACETONITRILE, AND ITS APPLICATION TO THE SYNTHESIS OF PHOSPHONIC-ACIDS AND VINYL PHOSPHATES [J].
MORITA, T ;
OKAMOTO, Y ;
SAKURAI, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (01) :267-273
[8]  
PHILLIPS AMM, IN PRESS J CHEM S P1
[9]   PHOSPHONIC SYSTEMS .2. FUNCTIONAL-GROUP AND SKELETON MODIFICATIONS IN DIETHYL ESTERS OF 2-PROPENYL (AND 2-PENTENYL) PHOSPHONIC-ACIDS [J].
PHILLIPS, AMMM ;
MODRO, TA .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 55 (1-4) :41-47
[10]   OLEFINIC STABILITY AND TAUTOMERIC EQUILIBRIA .1. BRANCHED-CHAIN UNSATURATED ESTERS [J].
RINEHART, KL ;
DOLBY, LJ .
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (01) :13-25