A convenient synthesis of arylmethylenecyclopropane carboxylic acids

✍ Scribed by A.W. Herriott; W.M. Jones

• Publisher: Elsevier Science
• Year: 1967
• Tongue: French
• Weight: 211 KB
• Volume: 8
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71612-1

✦ Synopsis

by basic hydrolysis is the standard method to prepare cyclopropene carboxylic acidst2).

We have found, however, that if the cyclopropene resulting from the initial addition has a benzylic hydrogen adjacent to the ring, the alkaline hydrolysis condition lead instead to methylenecyclopropane acids. This phenomenon which is apparently simply a result of a combination of the greater thermodynamic stability of the methylenecyclopropane relative to the cyclopropene and the acidity of the benzylic hydrogen allowed us to conveniently syn-