Thermal isomerization of dewarbenzene derivatives

✍ Scribed by Lorraine Ferrar; Mark Mis; Douglas R. Robello

• Book ID: 104095371
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 190 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.04.120

✦ Synopsis

The rates of thermal conversion of seven simple dewarbenzene derivatives to their corresponding benzene isomers were measured. Relatively minor substituent changes were found to have profound effects; isomerization rates increased with the number and strength of electron-withdrawing moieties. Surprisingly, the rate of thermal isomerization for one derivative was the same in fluid solution as in a solid polymer matrix, suggesting that this reaction has a low volume of activation. Other preliminary experiments suggest that the putative intermediate has some polar character. These data may provide some insights into the reaction mechanism.