✦ LIBER ✦

Intramolecular de Mayo Reactions of 3-Acetoxy-2-alkenyl-2-cyclohexenones. Preliminary communication

✍ Scribed by Wolfgang Oppolzer; T. Geoffrey C. Bird

Book ID: 102251917
Publisher: John Wiley and Sons
Year: 1979
Tongue: German
Weight: 217 KB
Volume: 62
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19790620429

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The photoaddition, hydrolysis, retro‐aldol sequences 1 → 2 → 3 and 4 → 5 + 6 → 7 proceeded in high yield and in a regiospecific manner. However, the enol acetate 8 on irradiation furnished the tricyclic ketoacetate 9 as the major product, presumably by a hydrogen shift in the intermediate diradical 11. Hydrolysis of the minor photoadduct 10 gave the dione 13.

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