Intramolecular  de Mayo  Reactions of 3‐Acetoxy‐2‐alkenyl‐2‐cyclohexenones. Preliminary communication | Zendy

Oppolzer Wolfgang | Zendy; Bird T. Geoffrey C. | Zendy

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

Author(s) -

Oppolzer Wolfgang,

Bird T. Geoffrey C.

Publication year - 1979

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19790620429

Subject(s) - chemistry , aldol reaction , hydrolysis , yield (engineering) , enol , diradical , aldol condensation , organic chemistry , enol ether , enone , medicinal chemistry , catalysis , singlet state , materials science , physics , nuclear physics , metallurgy , excited state

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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