Photochemical Reactions 127th CommunicationPhotochemistry of Epoxy-enones: Intramolecular Trapping of a Carbonyl Ylide

✍ Scribed by Shigeru Ohta; Bruno Frei; Oskar Jeger

• Book ID: 102857960
• Publisher: John Wiley and Sons
• Year: 1982
• Tongue: German
• Weight: 593 KB
• Volume: 65
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19820650802

✦ Synopsis

Abstract

On ^1^n, π* ‐excitation 5, 6‐epoxy‐2‐hydroxy‐5, 6‐dihydro‐β‐ionone ((E)‐4) shows the typical behaviour of a, β‐unsaturated γ, δ‐epoxy ketones undergoing primarily C(γ), O‐cleavage of the oxiran. However, ^1^π, π*‐excitation of (E)−4 leads to enol ether 10 which is formed by intramolecular insertion of the hydroxyl group of the ylide c.