Facile fragmentation of pinenes using dimethyl sulfoxide activated by phenyl dichlorophosphate or phosphorus oxychloride. Efficient conversion of α-pinene to carvone

✍ Scribed by Hsing-Jang Liu; James M Nyangulu

• Book ID: 104244571
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 140 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93456-2

✦ Synopsis

Treatment of pinenes with dimethyl sulfoxide in the presence of phenyl dichlorophosphate or phosphorus oxychloride resulted in facile fragmentation giving rise to limonene derivatives. The fragmentation reaction serves as a key step in the efficient conversion of a-pinene (1) to carvone (7).

Recently we reported the formation of 6-chloroalkyl Alcohols 6 could also be prepared directly from chloride 2 by treatment with silver oxide, potassium carbonate or sodium hydroxide. However, under a variety of conditions, the best yield obtained was only 30%.