FLUORINATED KETENE DITHIOACETALS .3. A RADICAL ENTRY TO ALPHA-PERFLUOROALKYL KETENE DITHIOACETALS - APPLICATION TO SUGAR-DERIVATIVES

被引：14

作者：

BERGERON, S ^{[1
]}

BRIGAUD, T ^{[1
]}

FOULARD, G ^{[1
]}

PLANTIERROYON, R ^{[1
]}

PORTELLA, C ^{[1
]}

机构：

[1] UFR SCI,CNRS,REARRANGEMENTS THERM & PHOTOCHIM LAB,BP 347,F-51062 REIMS,FRANCE

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 13期

关键词：

KETENE DITHIOACETALS; RADICAL PERFLUOROALKYLATION; PERFLUOROALKYLATED SUGARS;

D O I：

10.1016/S0040-4039(00)73028-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alpha-perfluoroalkyl ketene dithioacetals were synthesized by radical perfluoroalkylation of ketene dithioacetals with perfluoroalkyl iodide and sodium dithionite in a basic medium. Application to sugar derived ketene dithioacetals gave results depending strongly on the sugar structure.

引用

页码：1985 / 1988

页数：4

共 33 条

[21] TRIETHYLBORANE INDUCED PERFLUOROALKYLATION OF SILYL ENOL ETHERS OR GERMYL ENOL ETHERS WITH PERFLUOROALKYL IODIDES [J].

MIURA, K ;

TANIGUCHI, M ;

NOZAKI, K ;

OSHIMA, K ;

UTIMOTO, K .

TETRAHEDRON LETTERS, 1990, 31 (44) :6391-6394

[22] FLUORINATED KETENE DITHIOACETALS .2. SYNTHESIS OF 2-HYDROPERFLUORO ACID-DERIVATIVES FROM PERFLUOROKETENE DITHIOACETALS [J].

MUZARD, M ;

PORTELLA, C .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :29-31

[23]

MUZARD M, 1992, SYNTHESIS-STUTTGART, P965

[24] EFFECT OF REACTION CONDITIONS ON THE RADICAL-ADDITION OF PERFLUOROHEXYL IODIDE TO VINYL-ACETATE [J].

NAPOLI, M ;

FRACCARO, C ;

CONTE, L ;

GAMBARETTO, GP ;

LEGNARO, E .

JOURNAL OF FLUORINE CHEMISTRY, 1992, 57 (1-3) :219-227

[25] TRIFLUOROACETALDEHYDE THIOACETALS [J].

PURRINGTON, ST ;

SAMAHA, NF .

JOURNAL OF FLUORINE CHEMISTRY, 1989, 43 (02) :229-234

[26] ALKOXYPERFLUOROALKYLATION OF ENOL ETHERS CATALYZED BY IRON COMPLEXES [J].

SASAOKA, S ;

UNO, M ;

JOH, T ;

IMAZAKI, H ;

TAKAHASHI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (02) :86-87

[27] 2-(2,2,2-TRIFLUOROETHYLIDENE)-1,3-DITHIANES - NEW INTERMEDIATES FOR THE PREPARATION OF CF3-CONTAINING COMPOUNDS [J].

SOLBERG, J ;

BENNECHE, T ;

UNDHEIM, K .

ACTA CHEMICA SCANDINAVICA, 1989, 43 (01) :69-73

[28] NEW APPLICATIONS OF ORGANOFLUORINE REAGENTS IN ORGANIC-SYNTHESIS .5. PREPARATION AND SYNTHETIC UTILITY OF DIFLUOROKETENE THIOACETAL - NOVEL SYNTHETIC ROUTE TO ALPHA-MONOFLUOROALKANOIC ACIDS [J].

TANAKA, K ;

NAKAI, T ;

ISHIKAWA, N .

CHEMISTRY LETTERS, 1979, (02) :175-178

[29] ARENESELENOLATE-MEDIATED PERFLUOROALKYL-SULFENYLATION OF ENOL ETHERS [J].

UNEYAMA, K ;

KITAGAWA, K .

TETRAHEDRON LETTERS, 1991, 32 (28) :3385-3386

[30]

WAKSELMAN D, 1977, J CHEM SOC P1, P1365

← 1 2 3 4 →