Mercuric triflate-catalyzed reaction of propargyl acetates with water leading vinyl ketones

被引：38

作者：

Imagawa, H ^{[1
]}

Asai, Y ^{[1
]}

Takano, H ^{[1
]}

Hamagaki, H ^{[1
]}

Nishizawa, M ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Tokushima 7708514, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 03期

关键词：

D O I：

10.1021/ol0527431

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of propargyl acetate with water catalyzed by Hg(OTf)(2) afforded vinyl ketone as the major product along with a dimeric vinyl mercuric product and normal hydration products in small amounts. The reaction is an alternative to the Meyer-Schuster and Rupe rearrangement applicable to primary alcohols, although the mechanism is entirely different.

引用

页码：447 / 450

页数：4

共 38 条

[1] [Ru(η3-2-C3H4Me)(CO)(dppf)][SbF6]:: a mononuclear 16e- ruthenium(II) catalyst for propargylic substitution and isomerization of HCCCPh2(OH) [J].

Cadierno, V ;

Díez, J ;

García-Garrido, SE ;

Gimeno, J .

CHEMICAL COMMUNICATIONS, 2004, (23) :2716-2717

[2]

CAHIEZ G, 1977, SYNTHESIS-STUTTGART, P130

[3] TI/CU AND TI/AG CATALYSTS FOR THE ISOMERIZATION OF ALPHA-ACETYLENIC ALCOHOLS INTO ALPHA,BETA-ETHYLENIC CARBONYL DERIVATIVES [J].

CHABARDES, P .

TETRAHEDRON LETTERS, 1988, 29 (48) :6253-6256

[4] CHROMIUM PILLARED CLAY CATALYZED ALLYLIC OXIDATION AND OXIDATIVE DEPROTECTION OF ALLYL ETHERS AND AMINES - A SIMPLE AND CONVENIENT PROCEDURE [J].

CHOUDARY, BM ;

PRASAD, AD ;

SWAPNA, V ;

VALLI, VLK ;

BHUMA, V .

TETRAHEDRON, 1992, 48 (05) :953-962

[5] Biomimetic tandem cyclization catalyzed by Hg(OTf)2 affording polycarbocycles [J].

Imagawa, H ;

Iyenaga, T ;

Nishizawa, M .

SYNLETT, 2005, (04) :703-705

[6] Mercuric triflate-catalyzed tandem cyclization leading to polycarbocycles [J].

Imagawa, H ;

Iyenaga, T ;

Nishizawa, M .

ORGANIC LETTERS, 2005, 7 (03) :451-453

[7] Mercuric triflate-catalyzed synthesis of 2-methylfurans from 1-alkyn-5-ones [J].

Imagawa, H ;

Kurisaki, T ;

Nishizawa, M .

ORGANIC LETTERS, 2004, 6 (21) :3679-3681

[8] ORGANOMETALLIC CHEMISTRY IN INDUSTRIAL VITAMIN-A AND VITAMIN-E SYNTHESIS [J].

MERCIER, C ;

CHABARDES, P .

PURE AND APPLIED CHEMISTRY, 1994, 66 (07) :1509-1518

[9]

Meyer K.H., 1922, CHEM BER-RECL, V55, P819

[10] A NEW ELONGATION REACTION OF 3 CARBON UNITS [J].

MURAI, A ;

ABIKO, A ;

SHIMADA, N ;

MASAMUNE, T .

TETRAHEDRON LETTERS, 1984, 25 (43) :4951-4954

← 1 2 3 4 →