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Photoaddition of Tertiary Amines to 2‐Cyclopentylidenecyclopentanone
Author(s) -
Huang TianChyuan,
Ho TongIng
Publication year - 1993
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.199300087
Subject(s) - chemistry , cycloaddition , triethylamine , photochemistry , quantum yield , acetonitrile , adduct , yield (engineering) , electron transfer , quenching (fluorescence) , tertiary amine , organic chemistry , fluorescence , catalysis , physics , materials science , quantum mechanics , metallurgy
Photochemical reactions of 2‐cyclopentylidenecyclopentanone with diisopropylmethylamine, diisopropylethylamine, dimethylaniline, triethylamine, isopropyldimethylamine and dimethylbutylamine in acetonitrile were studied. Besides the addition product, a novel 3+2 cycloaddition adduct 3a‐hydroxytrispiro(octahydropentalene‐1,1′:2,1″:3,1‴‐triscyclopentane)‐2‴‐one was isolated. The quantum yield and Stern‐Volmer parameters with triplet quencher piperylene are reported. From these kinetic studies of mechanism photo‐induced electron transfer and proton transfer is proposed for formation of the novel 3+2 cycloadduct of 2‐cyclopentylidenecyclopentanone.