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Photochemical Reactions. 126th Communication. Photochemistry of an α, β: δ, ε‐unsaturated ketone: 4‐(2′, 7′, 7′‐Trimethylbicyclo [3.2.0]hept‐2′‐en‐1′‐yl)‐3‐buten‐2‐one
Author(s) -
Ishii Keitaro,
Lyle Terry A.,
Schweizer W. Bernd,
Frei Bruno
Publication year - 1982
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.19820650219
Subject(s) - chemistry , cycloaddition , photochemistry , ketone , intramolecular force , enol , enol ether , ether , yield (engineering) , medicinal chemistry , excitation , stereochemistry , organic chemistry , catalysis , materials science , metallurgy , electrical engineering , engineering
On 1 n,π*‐excitation, the title compound 2 undergoes a photoinduced intramolecular [4 + 2]‐cycloaddition affording the tetracyclic enol ether 3 as the only product in 79% yield. The assigned structure of 3 was confirmed by its conversion to the p ‐nitrobenzoate 6 whose structure was determined by X‐ray analysis.