Premium
Photochemical Rearrangements of 6‐Methoxymethylbicyclo[4.4.0]Dec‐1‐En‐3‐One and 6‐Methoxymethylbicyclo[4.3.0]Non‐1‐En‐3‐One
Author(s) -
Lai AnKuo,
Liao ChunChen
Publication year - 1992
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199200072
Subject(s) - chemistry , photochemistry , benzene , intramolecular force , yield (engineering) , irradiation , hydrogen atom abstraction , photodissociation , excitation , hydrogen , medicinal chemistry , stereochemistry , organic chemistry , materials science , physics , nuclear physics , electrical engineering , metallurgy , engineering
The irradiation of the title compounds 6 and 12 in isooctane and benzene was investigated. The photochemical reactions took place sluggishly upon n→π * excitation (λ > 300 nm) in deoxygenated solutions but more rapidly in the presence of air; deconjugation to yield β,γ‐unsaturated ketones and lumiketone rearrangement were the main primary photochemical reactions. In contrast, intramolecular hydrogen abstraction by the C α ‐carbon was the main reaction upon π→ * excitation (λ = 254 nm).