A one-pot synthesis of unsymmetrical and symmetrical tetrasubstituted alpha-fluoro-alpha beta-unsaturated esters

被引：12

作者：

Tsai, HJ ^{[1
]}

Thenappan, A ^{[1
]}

Burton, DJ ^{[1
]}

机构：

[1] UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1995年 / 105卷 / 1-4期

基金：

美国国家科学基金会;

关键词：

beta-ketophosphonates; betaine; phosgene; perfluorinated Grignard reagents; Emmons reaction; olefins;

D O I：

10.1080/10426509508042064

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Acylation of [(EtO)(2)P(O)CFCO(2)Et]Li--(+) 1 with acid chlorides RC(O)Cl or phosgene CIC(O)Cl and subsequent reaction of the acylated phosphonate with organometallic reagents (R'M) provide unsymmetrical and symmetrical tetrasubstituted alpha-fluoro-alpha,beta-unsaturated esters, RR'C=CFCO(2)Et and R(2)'=CFCO(2)Et, in moderate to good yields.

引用

页码：205 / 212

页数：8

共 4 条

[1] One-Pot Synthesis of α,β-Unsaturated Esters Promoted by Sodium Hydride
Swetha, M.
Ramana, P. Venkata
Shirodkar, S. G.
ASIAN JOURNAL OF CHEMISTRY, 2011, 23 (02) : 522 - 524
[2] Nitration of alpha,beta-unsaturated esters. Evidence for positive charge build-up adjacent to carbonyl carbon
Hewlins, SA
Murphy, JA
Lin, J
Hibbs, DE
Hursthouse, MB
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (10): : 1559 - 1570
[3] One-pot Wittig reaction for the synthesis of α,β-unsaturated esters using highly basic magnesium/lanthanum mixed oxide
Kantam, M. Lakshmi
Kumar, K. B. Shiva
Balasubramanyam, V.
Venkanna, G. T.
Figueras, F.
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2010, 321 (1-2) : 10 - 14
[4] Convenient One-Pot Two-Step Synthesis of Symmetrical and Unsymmetrical Diacyl Ureas, Acyl Urea/Carbamate/Thiocarbamate Derivatives, and Related Compounds
Hernandez, Anolan Garcia
Grooms, Gregory M.
El-Alfy, Abir T.
Stec, Jozef
SYNTHESIS-STUTTGART, 2017, 49 (10): : 2163 - 2176

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