PALLADIUM(II)-CATALYZED ACETALIZATION OF ALLYLIC ACETATES AND ITS UTILIZATION FOR THE SYNTHESIS OF 2-CYANOVINYL KETONES

被引：35

作者：

HOSOKAWA, T

AOKI, S

MURAHASHI, SI

机构：

[1] Department of Chemistry, Faculty of Engineering Science, Osaka University

来源：

SYNTHESIS-STUTTGART | 1992年 / 06期

关键词：

D O I：

10.1055/s-1992-26165

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alpha-cyanoallyl acetate (1a), when treated with methanol in the presence of bis(acetonitrile)dichloropalladium(II) catalyst, is acetalized at the terminal olefinic carbon to give 1-cyano-3,3-dimethoxypropyl acetate (2). Gamma-substituted alpha-cyanoallyl acetates give 3-substituted 1-cyano-3-oxo-propyl acetates 5 from which 2-cyanovinyl ketones 11 are obtained in good yields,

引用

收藏

页码：558 / 561

页数：4

相关论文

共 18 条

[1] (BETA-AMINOACYL)PALLADIUM(II) COMPLEXES - PREPARATIONS, STRUCTURES, AND REACTIONS [J].

HEGEDUS, LS ;

ANDERSON, OP ;

ZETTERBERG, K ;

ALLEN, G ;

SIIRALAHANSEN, K ;

OLSEN, DJ ;

PACKARD, AB .

INORGANIC CHEMISTRY, 1977, 16 (08) :1887-1894

[2]

Henry P. M., 1980, PALLADIUM CATALYZED

[3] PALLADIUM(II)-CATALYZED OXIDATION OF CARBON-CARBON DOUBLE-BONDS OF ALLYLIC COMPOUNDS WITH MOLECULAR-OXYGEN - REGIOSELECTIVE FORMATION OF ALDEHYDES [J].

HOSOKAWA, T ;

AOKI, S ;

TAKANO, M ;

NAKAHIRA, T ;

YOSHIDA, Y ;

MURAHASHI, SI .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (21) :1559-1560

[4] NEW ASPECTS OF OXYPALLADATION OF ALKENES [J].

HOSOKAWA, T ;

MURAHASHI, SI .

ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (02) :49-54

[5] PALLADIUM(II)-CATALYZED ACETALIZATION OF TERMINAL OLEFINS BEARING ELECTRON-WITHDRAWING SUBSTITUENTS WITH OPTICALLY-ACTIVE DIOLS [J].

HOSOKAWA, T ;

OHTA, T ;

KANAYAMA, S ;

MURAHASHI, SI .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (09) :1758-1764

[6] CATALYSIS OF PD(II)-CATALYZED ACETALIZATION OF ALKENES WITH DIOLS [J].

HOSOKAWA, T ;

ATAKA, Y ;

MURAHASHI, SI .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (01) :166-169

[7]

HUNT DF, 1972, TETRAHEDRON LETT, P3595

[8] COPPER(I) CHLORIDE [J].

KELLER, RN ;

WYCOFF, HD .

INORGANIC SYNTHESES, 1946, 2 :1-4

[9] OXIDATIONS OF OLEFINS WITH ALCOHOLIC PALLADIUM(II) SALTS [J].

LLOYD, WG ;

LUBEROFF, BJ .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (12) :3949-&

[10] PALLADIUM-CATALYZED REARRANGEMENT OF ALPHA-CYANOALLYLIC ACETATES APPLICATION TO A NEW SYNTHETIC METHOD FOR FURANS [J].

MANDAI, T ;

HASHIO, S ;

GOTO, J ;

KAWADA, M .

TETRAHEDRON LETTERS, 1981, 22 (23) :2187-2190