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Photochemistry of 8,8,9,9‐tetramethyl‐1,3,4,6,7,8‐hexahydro‐1,4‐ethanonaphthalene‐2,5‐dione, a δ‐oxo‐β,γ‐unsaturated ketone
Author(s) -
Kilger Ralf,
Körner Wolfgang,
Margaretha Paul
Publication year - 1984
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.19840670611
Subject(s) - chemistry , benzene , acetone , ketone , xanthone , dodecane , photochemistry , excitation , methane , medicinal chemistry , irradiation , organic chemistry , physics , nuclear physics , electrical engineering , engineering
The oxa‐di‐π‐methane rearrangement product 4,4,9,9‐tetramethyltetracyclo [6.4.0.0 1,5 .0 2,8 ]dodecane‐7,12‐dione ( 2 ) is formed selectively in a variety of solvents on either direct (λLD = 254, 300, 350 nm) or sensitized (xanthone, acetone, benzene) irradiation of the title compound 1 . The efficiency for this rearrangement is higher on S o –S 1 excitation (Φ −1 = 0.67) than on either S o –S 2 or S o –S 3 excitation (Φ −1 = 0.58).