A rearrangement of 1-hydroperoxy-2-oxabicycloalkanes into lactones of ω-acyloxy-(ω-3)-hydroxyalkanoic acids related to the Criegee reaction

✍ Scribed by Yuri N Ogibin; Alexandre O Terent'ev; Alexandre V Kutkin; Gennady I Nikishin

• Book ID: 104232408
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 124 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)02368-1

✦ Synopsis

1-Hydroperoxy-2-oxabicyclo[n.4.0]alkanes (n=3, 4, 5 and 10) on heating with formic or acetic acid containing a catalytic amount of sulfuric acid undergo a rearrangement into lactones of v-acyloxy-(v-3)-hydroxyalkanoic acids by a mechanism related to the Criegee reaction.