The lewis acid catalyzed reaction of 3-butyn-2-one with alkenes

✍ Scribed by Barry B. Snider; Louis A. Brown; Robin S. Eichen Conn; Thomas A. Killinger

• Book ID: 104235386
• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 219 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)83086-0

✦ Synopsis

We have recently shown that the aluminum chloride catalyzed reaction of propiolate esters with alkenes yields stereospecific [2+23 cycloadducts and/or ene adducts, depending on the degree of substitution of the double bond?sUnlike other aluminum chloride catalyzed [2+2] cycloaddition reactions of acetylenes,3 this reaction appears to involve complexation of the Lewis acid with the carbomethoxy group rather than the acetylene. It should, therefore, be generalizable to acetylenes containing other electron withdrawing groups capable of complexing with Lewis acids.

In this paper, we report the Lewis acid catalyzed reaction of 3-butyn-a-one' with alkenes to provide a variety of interesting 2,5-dienones, 2,4-dienones, and 1-cyclobutenyl methyl ketones which were previously difficult to prepare. The