Nucleophilic substitutions at ozonides

✍ Scribed by Karl Griesbaum; Willi Volpp; Tae-Seong Huh

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 110 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)99504-2

✦ Synopsis

Reactions of 3-acetoxy-3,5,5-trimethyl-1,2,4-trioxolane (z) with methanol, benzyl alcohol or phenol gave the corresponding ether ozonldes z -e. Reaction of 2 with benzyl alcohol and with acetate ion gave 5d and 2, respectfiely. -The known reactions of nucleophiles with ozonides 1 occur either by attack at the peroxide bridge and formation of fragments 2 and 2 or by attack at a CH-bond of the 1,2,4-trioxolane ring and formation of fragments 2 and i'. Nucleophilic substitutions at the C-atoms of the 1,2,4-trioxolane system with retention of the ring are not known.