Room Temperature Acylketene Formation? 1,3-Dioxin-4-ones via Silver(I) Activation of Phenylthioacetoacetate in the Presence of Ketones

被引：11

作者：

May, Aaron E. ^{[1
]}

Hoye, Thomas R. ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 17期

基金：

美国国家卫生研究院;

关键词：

ALPHA-OXO KETENES; 2,2,6-TRIMETHYL-4H-1,3-DIOXIN-4-ONE; ACETYLKETENE; PHOTOLYSIS; ESTERS;

D O I：

10.1021/jo101372v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Silver(I) activation of thioacetoacetates in the presence of ketones produces 1,3-dioxin-4-ones. Mechanistic studies addressing the intermediacy of an acylketene intermediate are described.

引用

页码：6054 / 6056

页数：3

共 17 条

[1] Sodium carbonate as a solid-phase reagent for the generation of acetylketene [J].

Bell, Kelcey ;

Sadasivam, Dhandapani V. ;

Gudipati, Indra Reddy ;

Ji, Hua ;

Birney, David .

TETRAHEDRON LETTERS, 2009, 50 (12) :1295-1297

[2] Chemoselectivity in the reactions of acetylketene and acetimidoylketene: Confirmation of theoretical predictions [J].

Birney, DM ;

Xu, XL ;

Ham, S ;

Huang, XM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7114-7120

[3] PREPARATION OF ACYLTETRONIC ACIDS USING TERT-BUTYL ACETOTHIOACETATE - TOTAL SYNTHESIS OF THE FUNGAL METABOLITES CAROLIC, CARLOSIC, AND CARLIC ACIDS [J].

BOOTH, PM ;

FOX, CMJ ;

LEY, SV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :121-129

[4] Flash photolysis of 2,2,6-trimethyl-4H-1,3-dioxin-4-one in aqueous solution: Hydration of acetylketene and ketonization of acetoacetic acid enol [J].

Chiang, Y ;

Guo, HX ;

Kresge, AJ ;

Tee, OS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (14) :3386-3391

[5] ACETOACETYLATION WITH "2,2,6-TRIMETHYL-4H-1,3-DIOXIN-4-ONE - A CONVENIENT ALTERNATIVE TO DIKETENE [J].

CLEMENS, RJ ;

HYATT, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (14) :2431-2435

[6]

Douglas K.T., 1980, J. Chem. Soc., V15, P728

[7] AN UNUSUAL ELIMINATION ADDITION (KETEN-MEDIATED) AMINOLYSIS PATHWAY FOR MALONIC S-THIOESTERS, INCLUDING S-MALONYL COENZYME-A [J].

DOUGLAS, KT ;

ALBORZ, M ;

RULLO, GR ;

YAGGI, NF .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (04) :245-246

[8] DIRECT OBSERVATION OF ALPHA-OXO KETENES FORMED FROM 1,3-DIOXIN-4-ONES AND THE ENOLS OF BETA-KETO-ESTERS [J].

FREIERMUTH, B ;

WENTRUP, C .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2286-2289

[9] DIE PRAPARATIVE BEDEUTUNG DER ZERSETZUNG VON DIAZO-CARBONYLVERBINDUNGEN IM UV-LICHT [J].

HORNER, L ;

SPIETSCHKA, E .

CHEMISCHE BERICHTE-RECUEIL, 1952, 85 (03) :225-229

[10] Dual Macrolactonization/Pyran-Hemiketal Formation via Acylketenes: Applications to the Synthesis of (-)-Callipeltoside A and a Lyngbyaloside B Model System [J].

Hoye, Thomas R. ;

Danielson, Michael E. ;

May, Aaron E. ;

Zhao, Hongyu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (50) :9743-9746

← 1 2 →