Synthesis of fluoroalkyl-δ-lactones from polyfluoroalkyl iodides and 5-hexenoic acids

被引：12

作者：

Fang, Xiang ^{[1
,2
]}

Ying, Qi ^{[1
,2
]}

Chen, Yang ^{[1
,2
]}

Yang, Xueyan ^{[1
,2
]}

Yang, Xianjin ^{[1
,2
,3
]}

Wu, Fanhong ^{[1
,2
,3
]}

机构：

[1] E China Univ Sci & Technol, Sch Chem & Mol Engn, Adv Mat Lab, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2008年 / 129卷 / 04期

基金：

中国国家自然科学基金;

关键词：

5-hexenoic acids; polyfluoroalkyl iodide; delta-valerolactone; sodium dithionite; polyfluoroalkyl-lactonization;

D O I：

10.1016/j.jfluchem.2007.12.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The polyfluoroalkyl-lactonization of 5-hexenoic acids with the polyfluoroalkyl iodides initiated by sodium dithionite was carried out in aqueous acetonitrile, providing an efficient method for the synthesis of fluorine-containing 8-valerolactones. Formation of RfCH2CH = CH(CH2)(2)COOH appeared to be unexpected minor product in sulfinatodehalogenation reagents. (C) 2008 Elsevier B.V. All rights reserved.

引用

收藏

页码：280 / 285

页数：6

相关论文

共 19 条

[1] ON THE CONVERSION OF DIHYDROARTEMISINIC ACID INTO ARTEMISININ [J].

ACTON, N ;

ROTH, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3610-3614

[2] METHYL (3R)-3-HYDROXYHEX-5-ENOATE AS A PRECURSOR TO CHIRAL MEVINIC ACID ANALOGS [J].

BENNETT, F ;

KNIGHT, DW ;

FENTON, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :133-140

[3] LACTONE FORMATION IN FREE-RADICAL ADDITION OF IODOPERFLUOROALKANES TO ALKENOIC ACIDS + ESTERS [J].

BRACE, NO .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (05) :1247-&

[4] Syntheses with perfluoroalkyl iodides.: A review -: Part III.: Addition of RFI to norbornene esters, acids and anhydrides, alkenoic acids and esters, alkenylsuccinic anhydrides or diesters, and to vinyl monomers;: lactonization and other reactions of adducts;: hydroperfluoroalkylation by RFI;: synthesis and reactions of I(CF2)nI homologues (n=1-3);: perfluoroalkylation of arenes by RFI or [RFCO2]2;: RFI in the synthesis of RFSR and segmented RF(CH2)nSH;: and, useful derivatives therefrom [J].

Brace, NO .

JOURNAL OF FLUORINE CHEMISTRY, 2001, 108 (02) :147-175

[5] FACILE ELIMINATION OF FLUORIDE ION IN DEHYDROHALOGENATION OF 3-IODO-4-(PERFLUOROALKYL)BUTANOIC ACIDS - PREPARATION OF FLUORINATED SORBIC ACID ANALOGS [J].

BRACE, NO .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (14) :1904-&

[6] LONG CHAIN ALKANOIC AND ALKENOIC ACIDS WITH PERFLUOROALKYL TERMINAL SEGMENTS [J].

BRACE, NO .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (12) :4491-&

[7]

BRACE NO, 1984, 4 INT S ORG FREE RAD

[8] STUDIES ON FLUOROALKYLATION AND FLUOROALKOXYLATION .3. PERFLUOROALKYLATION OF OLEFINS WITH PERFLUOROALKYL IODIDES AND COPPER IN VARIOUS SOLVENTS [J].

CHEN, QY ;

YANG, ZY .

JOURNAL OF FLUORINE CHEMISTRY, 1985, 28 (04) :399-411

[9]

CHEN ZY, 1989, J FLUORINE CHEM, V45, P435

[10]

CONLEY RT, 1966, INFRARED SPECTROSCOP, P143