DIRECT FORMATION OF REACTIVE ALKYNYLTRICHLOROTINS FROM 1-ALKYNES, SNCL4, AND BU3N - A MILD ALKYNYLATION REAGENT OF ALDEHYDES, ACETALS, AND ENONES

被引：33

作者：

YAMAGUCHI, M

HAYASHI, A

HIRAMA, M

机构：

来源：

CHEMISTRY LETTERS | 1992年 / 12期

关键词：

D O I：

10.1246/cl.1992.2479

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A reagent system of 1-alkyne, SnCl4, and Bu3N alkynylates aldehydes, acetals, and enones under mild reaction conditions giving acetylenic alcohols, acetylenic ethers, and acetylenic ketones, respectively, in high yields. Alkynyltrichlorotins are shown to be the reactive species for these reactions.

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页码：2479 / 2482

页数：4

相关论文

共 17 条

[1]

BOGORADOVSKII ET, 1975, J GEN CHEM USSR, V45, P1620

[2] BORON-TRIFLUORIDE ETHERATE MEDIATED 1,4-ADDITION OF (1-ALKYNYL)DIISOPROPOXYBORANES TO ALPHA,BETA-UNSATURATED KETONES - A CONVENIENT NEW ROUTE TO 3-ALKYNYL KETONE SYNTHESIS [J].

FUJISHIMA, H ;

TAKADA, E ;

HARA, S ;

SUZUKI, A .

CHEMISTRY LETTERS, 1992, (04) :695-698

[3] REVERSIBLE CROTYLSTANNATION OF CARBONYL-COMPOUNDS - CROTYLSTANNATION ABILITY OF BU3-NCLNSNCH2CH=CHCH3(N=0,1,2) COMPOUNDS TOWARDS ACETONE AND BENZALDEHYDE AND C-13 NMR CHARACTERIZATION [J].

GAMBARO, A ;

MARTON, D ;

PERUZZO, V ;

TAGLIAVINI, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 204 (02) :191-196

[4] ALLYLBUTYLTIN HALIDES (CH2=CHCH2)SNBU3-NCLN(N=0,1,2,3) - PREPARATION, C-13 NMR CHARACTERIZATION AND ALLYLSTANNYLATION ABILITY TOWARDS KETONES AND ALDEHYDES [J].

GAMBARO, A ;

PERUZZO, V ;

PLAZZOGNA, G ;

TAGLIAVINI, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 197 (01) :45-50

[5]

Harrison P.G., 1982, COMPREHENSIVE ORGANO, V2, P629

[6] A CONVENIENT METHOD FOR THE PREPARATION OF SECONDARY PROPARGYLIC ETHERS - THE REACTION OF ACETALS WITH 1-TRIMETHYLSILYLALKYNES PROMOTED BY THE COMBINED USE OF CATALYTIC AMOUNTS OF TIN(IV) CHLORIDE AND ZINC-CHLORIDE [J].

HAYASHI, M ;

INUBUSHI, A ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1987, (10) :1975-1978

[7] A CONVENIENT METHOD FOR THE PREPARATION OF SECONDARY PROPARGYLIC ETHERS - THE REACTIONS OF ACETALS WITH 1-TRIMETHYLSILYL-1-ALKYNES PROMOTED BY THE COMBINED USE OF CATALYTIC AMOUNTS OF TIN(IV) CHLORIDE AND ZINC-CHLORIDE [J].

HAYASHI, M ;

INUBUSHI, A ;

MUKAIYAMA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (11) :4037-4042

[8] ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .4. REACTIONS WITH SILYLACETYLENIC COMPOUNDS - FORMATION OF CHIRAL PROPARGYLIC ALCOHOLS [J].

JOHNSON, WS ;

ELLIOTT, R ;

ELLIOTT, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2904-2905

[9]

KLEINER FG, 1968, LIEBIGS ANN CHEM, V716, P19

[10]

KOMAROV NV, 1982, DOKL AKAD NAUK SSSR, V261, P103