Attempted Synthesis of Hexamethylfulvene

✍ Scribed by D. Dimaio; N.S. Mills; A. Gum; S. Mosser

• Book ID: 102614825
• Publisher: Elsevier Science
• Year: 1993
• Tongue: English
• Weight: 229 KB
• Volume: 47
• Category: Article
• ISSN: 0026-265X
• DOI: 10.1006/mchj.1993.1028

✦ Synopsis

Synthesis of hexamethylfulvene by addition of isopropyl magnesium chloride to methoxyprotected tetramethylcyclopentadienone followed by acid-catalyzed dehydration/ deprotection resulted in formation of two isomers of the desired hexamethylfulvene. The intermediate leading to the isomeric products was isolated and a mechanism for their formation proposed. Attempts to isomerize the isomeric products resulted in dimerization with no apparent isomerization. AMI molecular orbital calculations on the isomers of hexamethylfulvene reveal that the desired isomer is not the most stable, suggesting that exploration of further isomerization routes will not result in the desired isomer. 1993 Academic Press, Inc.