Photochemistry

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Photolysis of 1,1,4,4-tetramethyl2,3-tetralindione (23) has been investigated 60) in a variety of solvents. 265 M. B. R u b i n One of the byproducts observed in some cases was tetramethylindanone (24) ; in acetic acid it constituted 6% and in benzene 14% of the total product. The most reasonable mechanism for formation of 24 is via cleavage and decarbonylation to give the tertiary-benzilic diradical 25 which can cyclize to 24. The process may be facilitated by the considerable stabilization present in 25.

Bd. 13/2, 259 M. B. Rubin Hammond and collaborators as part of their extensive studies on photosensitized reactions. Examples include (a) cis-trans isomerization of olefins sensitized b y biacetyl 42,64,65,176), 2,3-pentanedione 64,65), benzil 64,65,89) a_ and fl-naphil ~4), and phenanthrenequinone 30,65) (b) diene and anthracene dimerizations sensitized b y biacetyl 9,45,94), 2,3-pentanedione 94,162), camphorquinone 94), benzil 9a,162), and flnaphthil 94), and (c) the quadricyclene-norbornadiene interconversion sensitized 6e) b y benzil.

This ratio decreased with increasing temperature; phosphorescence was completely quenched by added oxygen 114). cr exhibit the unusual and very useful (vide infra) property of fluorescence and phosphorescence in fluid solution. The intensity of phosphorescence was not appreciably affected 58) by variations in viscosity in a series of hydrocarbon solvents but appears to be dependent on a variety of factors including solvent 7,125,141), light intensity, temperature, and the presence of impurities.

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