
TY  - JOUR
A1  - Teitei, T 
A1  - Wells, D 
A1  - Sasse, WHF 
T1  - Photochemical syntheses. VII. The formation of 1,2-Diaryl-8b-methoxy-2a,8b-dihydrocyclobuta[a]naphthalenes in photoadditions involving 1-methoxy-naphthalene and heterocyclic diarylacetylenes
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1973
VL  - 26
IS  - 10
SP  - 2129
EP  - 2146
KW  - 
UR  - https://doi.org/10.1071/CH9732129 
N2  - The diarylacetylenes (2), (3), (4), (9, (6), and (7) react with 1- methoxynaphthalene on ultraviolet irradiation to give 1,2-diaryl-8b- methoxy-2a,8b-dihydrocyclobuta[a]-naphthalenes (d) and/or (d?). Phenyl(4-pyridyl)acetylene (2), phenyl(3-pyridyl)-acetylene (3), di(3- pyridyl)acetylene (5) and phenyl(2-furyl)acetylene (6) also give tetracyclic photoadducts (c) and/or (c?). The major product of the reaction with (2) is a benzo[h]isoquinoline which is formed by photodehydrocyclization of (2d) and for which structure (2f) is proposed on spectral grounds. Similarly (3) gives a benzo[f]-quinoline (3g) and two benzo[h]quinolines (3h) and (3h?).     Thermolysis of (3c) and (3c?) gives (3e) and (3e?), respectively. These isomerizations are quantitatively reversed by ultraviolet irradiation but irradiation of (3d) and (3d?) gives mixtures containing (3h), (3h?), (3c), and (3c?). Di(3-pyridyl)acetylene (5) forms with naphthalene the photoadduct (5a). 
ER  -

