
TY  - JOUR
A1  - Collins, DJ 
A1  - Hobbs, JJ 
T1  - The influence of copper halides on the course of photolysis of &#945;,&#945;&#8242;-Disubstituted stilbenes
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1967
VL  - 20
IS  - 9
SP  - 1905
EP  - 1920
KW  - 
UR  - https://doi.org/10.1071/CH9671905 
N2  - Photolysis of 4,4?-dimethoxy-&#945;,&#945;?-dimethylstilbene (Id) in the presence of air, in cyclohexane containing iodine (Method A), gave an abnormally low yield (11%) of 3,6-dimethoxy-9,10-dimethylphenanthrene (IId), together with 9% of p-methoxy-acetophenone formed by photooxidative fission. Irradiation of (Id) in the presence of air in absolute ethanol containing iodine and cupric chloride (or bromide) (Method B), afforded a significantly higher yield (54%) of (IId), while a similar reaction in which cupric chloride was omitted produced only 0.6% of (IId). The yields of phenanthrenes obtained by photolysis by Methods A and B of various &#945;,&#945;?-disubstituted, &#945;-monosubstituted, and &#945;-unsubstituted stilbenes are compared.   The nature of the photooxidative cleavage of (Id) (using Method A), and the possible role of cupric and/or cuprous ions in facilitating the photoconversion of (Id) into (IId), are discussed.   Demethylation of (IId), (IIe), and (IIf) afforded the phenanthrene diols (IIa), (IIb), and (IIc), respectively. 
ER  -

