Acid-catalyzed aldehyde-ketone rearrangements in the gas phase. Cyclopentane- and cyclohexanecarboxaldehyde.

✍ Scribed by Pierluigi Giacomello; Adriano Pizzabiocca; Gabriele Renzi; Maurizio Speranza

• Book ID: 104221608
• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 247 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)88287-8

✦ Synopsis

Protonation by gaseous Hi, CnHi (n=1,2), s-C3HG and t-C H+ 49 cations promotes rearrangement of cyclopentane-and cyclohexanecarboxaldehyde to cyclohexanone and cyclo~entylmethyl ketone, respectively. The reaction was investigated by radiolytic and mass spectrometric methods. The mechanism of the acid-catalyzed rearrangement of aldehydes to ketones has long been studied in solution with somewhat puzzling results, owing irter alia to the fact that the carbonium ions iormed, following protonation at the carbonyl group and alkyl migration, can rapidly :8) see Proctor, C.