
TY  - JOUR
A1  - Beckwith, PLM 
A1  - Ghisalberti, EL 
A1  - Jefferies, PR 
A1  - Raston, CL 
A1  - White, AH 
T1  - A Study of the Photochemistry of Benzobicyclo[2.2.2]octan-2-ones
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1988
VL  - 41
IS  - 3
SP  - 351
EP  - 364
KW  - 
UR  - https://doi.org/10.1071/CH9880351 
N2  - The anti- and syn-3-methyl isomers of 5,8-dimethoxy-1,3-dimethyl-3,4-dihydro-1,4-ethanonaphthalen-2(1H)-one (2) and (3) and the 1,3,3- trimethyl analogue (4) were prepared from the Diels -Alder adduct of benzoquinone and 1,3-dimethylcyclohexadiene. The photochemistry of each has been studied and the structures of several photoproducts have been assigned. One of the products from irradiation of (3) was found by X-ray analysis to be a 1,4-disubstituted 1,2,3,4- tetrahydronaphthalene [methyl 2-(5&#8242;,8&#8242;-dimethoxy-4z&#8242;-methyl-1&#8242;,2&#8242;,3&#8242;,4&#8242;-tetrahydronaphthalen-1&#8242;-yl) propanoate ] with the unexpected cis-stereochemistry (11). Irradiation of (4) produces, inter alia, a compound containing the unusual tetracyclo [7.4.0.02,7.04,8] trideca -1(9),10,12-triene skeleton whose structure was determined by n.m.r. spectroscopy. 
ER  -

