37166-49-7

Upstream product

• 4526-07-2 1,4-bis(trimethylsilyl)-1,3-butadiyne 
• 874-60-2 4-methyl-benzoyl chloride 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 37176-83-3 1,10-Di-p-tolyl-deca-2,4,6,8-tetrain-1,10-dion 
• 37176-78-6 Butadiynyl-p-tolyl-keton 

Relevant academic research and scientific papers

Friedel-crafts reactions of bis(trimethylsilyl)polyynes with acyl chlorides; a useful route to terminal-alkynyl ketones

Bis(trimethylsilyl)acetylenes, Me3Si(CC)nSiMe3, react with acyl chloride-aluminium chloride complexes, XC6H4 COCl·AlCl3 in methylene chloride at 0-20° to form the corresponding ketones XC6H4CO(CC)nSiMe3 in excellent (n = 1) or moderate (n = 2, 4) yield. Treatment of the products with aqueous methanolic borax results in virtually quantitative liberation of the terminal alkynyl ketones XC6H4CO(CC)nH. The method provides the first practical route to the ketotetraynes (n = 4) and usefully supplements existing oxidative methods for keto-monoyne and -diyne synthesis. The oxalyl chloride-aluminium chloride complex reacts with Me3SiCCSiMe3 to give the novel silyl-substituted heterocycle (I): {A figure is presented}.