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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.
H .... C~ and allylic carbonium ions are energetically much more favorable than positive charge adjacent to a carbonyl or nitrile group in qualitative agreement with the overall trends and the substituent effects observed. 3. The Semidione Radical The inference that semidione radicals are intermediates in diketone photolysis has been widely accepted for m a n y years since it provides a satisfactory rationale for the results observed in m a n y reactions. Recently, direct evidence for the presence of these radicals has been obtained from flash photolysis x3) of benzil in alcoholic solvents and esr studie of irradiated solutions of biacetyl 12,171,1s3), camphorquinone 99,183), and other diones 183).
Rubin Both polar and steric factors play a role in determining the orientation of coupling with the semidione radical. The steric factor is illustrated in the reactions of camphorquinone with aldehydes. Aromatic aldehydes, butyraldehyde and pivalaldehyde reacted 15,130) exclusively to give 1,4adducts but acetaldehyde gave a mixture of both 1,2- and 1,4-adducts. The importance of polar factors was shown a24) in a series of reactions of substituted toluenes with plienanthrenequinone under irreversible conditions (4358/~).
