Kinetics of 2+2 cycloadditions of diphenylketene to enol ethers; The structure of the orientation complexes

✍ Scribed by Rolf Huisgen; Herbert Mayr

• Book ID: 104214953
• Publisher: Elsevier Science
• Year: 1975
• Tongue: French
• Weight: 208 KB
• Volume: 16
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75045-3

✦ Synopsis

Diphenylketene

combines stereospecifically with @-and tmns-propenyl propyl ether to produce 4-methyl-2,2diphenyI-3-propoxy-cyclobutanones ; the cis'enol ether reacts 170 times faster than the tmns isomer. ' This impressive cis preference was later observed in further ketene cycloadditions, 2-5 but appears to be unknown in other areas of olefinic reactivity.