The thermal decarboxylation of trans-2-phenylcyclopropyl-1-acetic acid

✍ Scribed by James J. Sims; Matt Ban

• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 158 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75366-4

✦ Synopsis

It has recently been demonstrated that cyclopropylacetic acid and 8-e of its derivatives will undergo smooth thermal decarboxylation with attendant opening of the cyclopropane ring (la-c). We have been investigating other possible cases of this new reaction to assess its value as a synthetic method. Several other compounds have behaved as expected (2) but one compound, trans-2-phenylcyclopropyl-l-acetic acid (3), 1, has given the unexpected results described herein.

When &was heated to 320' (bath temperature, N2, 735 arm) carbon dioxide evolution commenced and became vigorous at 330°. After two hours, 22% of the starting material was recovered unchanged. The neutral material produced contained three hydrocarbons 2 (7X), 2 (14%)~ 4 (12%) aad a y-lactone 2 (65%).