EXTREMELY SIMPLE ROUTE TO BETA-FLUORO VINAMIDINIUM SALTS - A NOVEL REACTION OF (POLYFLUORO-1-PROPENYL)TRIMETHYLAMMONIUM IODIDES WITH PRIMARY OR SECONDARY-AMINES

被引:26
作者
YAMANAKA, H
YAMASHITA, S
ISHIHARA, T
机构
[1] Department of Chemistry and Materials Technology, Kyoto Institute of Technology Matsugasaki, Sakyo-ku, Kyoto
关键词
BETA-FLUORO VINAMIDINIUM SALTS; FLUORINATED AMMONIUM SALTS; ALLYLIC SUBSTITUTION; N-N EXCHANGE REACTION;
D O I
10.1016/S0040-4039(00)74130-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(2,3,3-Trifluoro-1-propenyl)trimethylammonium iodide readily underwent demethylation-allylic substitution followed by N-N exchange reaction at ambient temperature or at 70-degrees-C by the action of various secondary amines or several primary amines to give the corresponding beta-fluorinated vinamidinium salts in good yields.
引用
收藏
页码:357 / 360
页数:4
相关论文
共 28 条
[1]   BROMINATION OF PUSH-PULL-OLEFINS .2. STRUCTURE ELUCIDATION OF BROMINATION PRODUCTS [J].
BURGI, D ;
STERCHI, A ;
NEUENSCHWANDER, M .
HELVETICA CHIMICA ACTA, 1977, 60 (07) :2195-2207
[2]   NUCLEAR MAGNETIC-RESONANCE INVESTIGATIONS OF IMINIUM ION INTERMEDIATES .9. MULTI-NUCLEAR STUDY OF THE REACTION BETWEEN LEWIS-ACIDS AND VINYLOGOUS AMIDES [J].
DORIE, J ;
GOUESNARD, JP ;
MARTIN, ML .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (06) :912-917
[3]  
ESCHENMOSER A, 1969, Pure and Applied Chemistry, V20, P1, DOI 10.1351/pac196920010001
[4]  
GOMPPER R, 1979, SYNTHESIS-STUTTGART, P213
[5]   THE REACTION OF ORGANOMETALLIC REAGENTS WITH UNSYMMETRICALLY SUBSTITUTED VINAMIDINIUM AND CHLOROPROPENIMINIUM SALTS [J].
GUPTON, JT ;
COURY, J ;
MOEBUS, M ;
FITZWATER, S .
SYNTHETIC COMMUNICATIONS, 1986, 16 (12) :1575-1586
[6]   THE REACTION OF 2-ARYLVINAMINDINIUM PERCHLORATES WITH SODIUM-BOROHYDRIDE AND SODIUM CYANOBOROHYDRIDE [J].
GUPTON, JT ;
ANDREW, SS ;
LIZZI, MJ .
SYNTHETIC COMMUNICATIONS, 1982, 12 (05) :361-371
[7]   THE PREPARATION AND SOME REACTIONS OF 2-(ARYLSULFONYL)VINAMIDINIUM SALTS [J].
GUPTON, JT ;
RIESINGER, SW ;
SHAH, AS ;
GALL, JE ;
BEVIRT, KM .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :976-980
[8]   REACTION OF 2-ARYL-3-(N,N-DIMETHYLAMINO)-1-PROPENES AND THEIR CORRESPONDING QUATERNARY AMMONIUM-SALTS WITH ORGANOMETALLIC SPECIES AND REDUCING AGENTS [J].
GUPTON, JT ;
LAYMAN, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) :3683-3686
[9]  
GUPTON JT, 1990, J ORG CHEM, V55, P735
[10]   O-N, S-N AND N-N EXCHANGE-REACTIONS AT OLEFINIC CARBON-ATOMS - FACILE SYNTHETIC METHOD FOR BETA-TRIFLUOROACETYLVINYLAMINES [J].
HOJO, M ;
MASUDA, R ;
OKADA, E ;
SAKAGUCHI, S ;
NARUMIYA, H ;
MORIMOTO, K .
TETRAHEDRON LETTERS, 1989, 30 (45) :6173-6176