The synthesis of 6-azabicyclo[7.3.1.]trideca-1(13),9,11-trien-5-one (4
) is described. Two routes to (4) based on the photolysis of N-[2-(3,4
-dimethoxyphenyl)ethyl]chloroacetamide (2b) and methylsiloxy-3-methoxy
phenyl)ethyl]chloroacetamide (2c) followed by O-demethylation or O-des
ilylation, were developed. Extension of the work has given the new m-c
yclophane ester derivative (9), whose structure has been confirmed by
X-ray crystallography.