A novel cyclopropanol formation

✍ Scribed by P.S. Venkataramani; William Reusch

• Book ID: 104215225
• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 165 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75364-0

✦ Synopsis

Reduction of unsaturated functi'ons by alkali metal in liquid ammonia solutions is a widely used synthetic method, ly2 and the large body of data regarding these reactions is in substantial agreement with currently accepted mechanistic rationalisations.3

In this communication we report an unexpected transformation of the enedione I which represents a new diversion in enone reductions.

Allylation of dihydroresorcinol followed by Michael addition of methyl vinyl ketone yielded a monocyclic triketone which was cyclized to I, mp 61.5-62.5, by the action of pyrrolidine.

The structure of I was supported by its analysis, infrared spectrum (vmax 1705,