Synthesis and intramolecular ring cleavage of 2-oxetanones

✍ Scribed by Keith T. Mead; Beverly Samuel

• Book ID: 104217842
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 221 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)82400-4

✦ Synopsis

Summar~~: Intermolecular 2 + 2 aldehyde-ketene cycloaddition, followed by Lewis acid induced intramolecular ring opening of the 2-oxetanone product have been used to prepare tetrahydrofuran and tetrahydropyran ring systems.

Among lactones, 2-oxetanones are characterized by their readiness to undergo ring-opening reactions.

Moreover, the variety of ways in which this can occur is the real mark of their versatility as synthetic intermediates.'