Selective fluorination of adamantanes by an electrochemical method

被引：22

作者：

Aoyama, Motoshi ^{[1
]}

Fukuhara, Tsuyoshi ^{[1
]}

Hara, Shoji ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Sapporo, Hokkaido 0608628, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 11期

关键词：

D O I：

10.1021/jo8004759

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective fluorination of adamantanes was achieved by the electrochemical fluorination method, using Et3N-5HF as electrolyte and a fluorine source. Mono-, di-, tri-, and tetrafluoroadamantanes were selectively prepared from adamantanes by controlling the oxidation potential, and the fluorine atoms were introduced selectively at the tertiary carbons. Adamantanes that have functional groups such as ester, cyano, and acetoxymethyl were also fluorinated selectively.

引用

页码：4186 / 4189

页数：4

共 46 条

[31] SYNTHETIC METHODS AND REACTIONS .91. IONIC FLUORINATION OF ADAMANTANE, DIAMANTANE, AND TRIPHENYLMETHANE WITH NO+BF4-/PYRIDINE POLYHYDROGEN FLUORIDE (PPHF) [J].

OLAH, GA ;

SHIH, JG ;

SINGH, BP ;

GUPTA, BGB .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (19) :3356-3358

[32]

OLAH GA, 1983, SYNTHESIS-STUTTGART, P713

[33] SYNTHETIC METHODS AND REACTIONS .63. PYRIDINIUM POLY-(HYDROGEN FLUORIDE) (30-PERCENT PYRIDINE 70-PERCENT HYDROGEN-FLUORIDE) - CONVENIENT REAGENT FOR ORGANIC FLUORINATION REACTIONS [J].

OLAH, GA ;

WELCH, JT ;

VANKAR, YD ;

NOJIMA, M ;

KEREKES, I ;

OLAH, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :3872-3881

[34] PREPARATION AND C-13 NMR SPECTROSCOPIC STUDY OF FLUOROADAMANTANES AND FLUORODIAMANTANES - STUDY OF C-13-F-19 NMR COUPLING-CONSTANTS [J].

OLAH, GA ;

SHIH, JG ;

KRISHNAMURTHY, VV ;

SINGH, BP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (16) :4492-4500

[35] 1,1,2,2-tetrafluoroethyl-N,N-dimethylamine:: a new selective fluorinating agent [J].

Petrov, VA ;

Swearingen, S ;

Hong, WP ;

Petersen, WC .

JOURNAL OF FLUORINE CHEMISTRY, 2001, 109 (01) :25-31

[36] ELECTROPHILIC ATTACK OF ELEMENTAL FLUORINE ON ORGANIC HALOGENS - SYNTHESIS OF FLUOROADAMANTANES [J].

ROZEN, S ;

BRAND, M .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (04) :733-736

[37] DIRECT SYNTHESIS OF FLUORO BICYCLIC COMPOUNDS WITH FLUORINE [J].

ROZEN, S ;

GAL, C .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2803-2807

[38]

Samnick S, 1997, J LABELLED COMPD RAD, V39, P241, DOI 10.1002/(SICI)1099-1344(199703)39:3<241::AID-JLCR966>3.3.CO

[39]

2-M

[40] FLUORINATION WITH CESIUM FLUOROXYSULFATE .11. MILD FUNCTIONALIZATION OF SATURATED-HYDROCARBONS [J].

STAVBER, S ;

ZUPAN, M .

TETRAHEDRON, 1989, 45 (09) :2737-2742

← 1 2 3 4 5 →