Premium
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 .