Friedel-crafts reactions of bis(trimethylsilyl)polyynes with acyl chlorides; a useful route to terminal-alkynyl ketones
作者： D.R.M. Walton , F. Waugh
DOI: 10.1016/S0022-328X(00)89260-8
关键词:
摘要: Abstract Bis(trimethylsilyl)acetylenes, Me 3 Si(CC) n SiMe , react with acyl chloride-aluminium chloride complexes, XC 6 H 4 COCl·AlCl in methylene at 0–20° to form the corresponding ketones CO(CC) excellent ( = 1) or moderate 2, 4) yield. Treatment of products aqueous methanolic borax results virtually quantitative liberation terminal alkynyl H. The method provides first practical route ketotetraynes and usefully supplements existing oxidative methods for keto-monoyne -diyne synthesis. oxalyl complex reacts SiCCSiMe give novel silyl-substituted heterocycle (I):
elsevier.com
sci-hub.se 参考文章(21)
U. Krüerke, Zur darstellung von äthinylsilanen Journal of Organometallic Chemistry. ,vol. 21, pp. 83- 90 ,(1970) , 10.1016/S0022-328X(00)90596-5
Leonhard Birkofer, Alfered Ritter, Heinz Uhlenbrauck, Substitutions‐ und Additionsreaktionen an silylierten Acetylenen Chemische Berichte. ,vol. 96, pp. 3280- 3288 ,(1963) , 10.1002/CBER.19630961226
Charles E. Castro, R. Havlin, V. K. Honwad, A. M. Malte, Steve W. Moje, Copper(I) substitutions. Scope and mechanism of cuprous acetylide substitutions Journal of the American Chemical Society. ,vol. 91, pp. 6464- 6470 ,(1969) , 10.1021/JA01051A049
Ferdinand Bohlmann, Peter Herbst, Ingeborg Dohrmann, Polyacetylenverbindungen, XLIV. Über neue Acetylenverbindungen aus der Gattung Chrysanthemum L. Chemische Berichte. ,vol. 96, pp. 226- 236 ,(1963) , 10.1002/CBER.19630960126
C. Eaborn, D.R.M. Walton, The alkali cleavage of some (phenylethynyl)-silanes and -germanes Journal of Organometallic Chemistry. ,vol. 4, pp. 217- 228 ,(1965) , 10.1016/S0022-328X(00)94162-7
Allan S. Hay, Oxidative Coupling of Acetylenes. II1 Journal of Organic Chemistry. ,vol. 27, pp. 3320- 3321 ,(1962) , 10.1021/JO01056A511
David H. Scheiber, The Preparation of Acetylenic Ketones Using Soluble Silver Acetylides Journal of the American Chemical Society. ,vol. 78, pp. 1675- 1678 ,(1956) , 10.1021/JA01589A050
R I Katkevich, Leontii I Vereshchagin, Advances in the Synthesis of α-Ethynylcarbonyl Compounds Russian Chemical Reviews. ,vol. 38, pp. 900- 912 ,(1969) , 10.1070/RC1969V038N11ABEH001861
Jean F. Normant, Monique Bourgain, Preparation de cetones α acetyleniques a partir d'acetylures cuivreux. Tetrahedron Letters. ,vol. 11, pp. 2659- 2662 ,(1970) , 10.1016/S0040-4039(01)98306-6
Alwyn G. Davies, R. J. Puddephatt, Organometallic reactions. Part X. The preparation and reactions of some alkynyl-lead compounds Journal of the Chemical Society C: Organic. pp. 317- 322 ,(1968) , 10.1039/J39680000317