Evidence for the intermediacy of an alkyne rather than an allene in the base-induced reaction of 3-bromo-6,7-benzobicyclo[3.2.1]octa-2,6-diene

✍ Scribed by Ferhan Türner; Yavuz Taşkesenligil; Metin Balci

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 405 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00592-x

✦ Synopsis

In order to reveal the real intermediate in the base-promoted reaction of 1, 2-methyl derivative 16 has been synthesized and its HBr elimination reaction studied. Reaction of 16 with potassium t-butoxide did not form the corresponding allene intermediate 17 under the same reaction conditions as described for 1. Under more drastic conditions exocyclic diene 18 was formed. These results provide evidence for the intermediacy of the alkyne 3 in the basepromoted reaction of 1.