A macrocyclic 2,19-dioxo[3.3](3,3´) azobenzolophane by transition-metal carbonyl complex-mediated CO insertion and cyclization

Schmiegel J, Grützmacher H-F (1990)
Chemische Berichte 123(8): 1749-1752.

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2,19-Dioxo[3.3](3,3´)azobenzolophane (5) has been obtained in a total yield of 18% by way of CO insertion and cyclization of 1,2-bis[3-(bromomethyl)phenyl]-4,4-dimethyl-3,5-pyrazoli-dinedione (1) using CO 2(CO) 8 in acetonitrile followed by the removal of the N-protecting 4,4-dimethylmalonyl groups. 5 is obtained predominantly as the trans / trans isomer 5a and can be isomerized by irradiation with [lambda]=369 nm to a mixture of nearly equal amounts of the trans / trans, cis / trans, and cis / cis isomers 5a, 5b and 5c. The thermal isomerization back to 5a is slow but fast upon irradiation with [lambda]=443 nm.
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Schmiegel J, Grützmacher H-F. A macrocyclic 2,19-dioxo[3.3](3,3´) azobenzolophane by transition-metal carbonyl complex-mediated CO insertion and cyclization. Chemische Berichte. 1990;123(8):1749-1752.
Schmiegel, J., & Grützmacher, H. - F. (1990). A macrocyclic 2,19-dioxo[3.3](3,3´) azobenzolophane by transition-metal carbonyl complex-mediated CO insertion and cyclization. Chemische Berichte, 123(8), 1749-1752.
Schmiegel, J., and Grützmacher, H. - F. (1990). A macrocyclic 2,19-dioxo[3.3](3,3´) azobenzolophane by transition-metal carbonyl complex-mediated CO insertion and cyclization. Chemische Berichte 123, 1749-1752.
Schmiegel, J., & Grützmacher, H.-F., 1990. A macrocyclic 2,19-dioxo[3.3](3,3´) azobenzolophane by transition-metal carbonyl complex-mediated CO insertion and cyclization. Chemische Berichte, 123(8), p 1749-1752.
J. Schmiegel and H.-F. Grützmacher, “A macrocyclic 2,19-dioxo[3.3](3,3´) azobenzolophane by transition-metal carbonyl complex-mediated CO insertion and cyclization”, Chemische Berichte, vol. 123, 1990, pp. 1749-1752.
Schmiegel, J., Grützmacher, H.-F.: A macrocyclic 2,19-dioxo[3.3](3,3´) azobenzolophane by transition-metal carbonyl complex-mediated CO insertion and cyclization. Chemische Berichte. 123, 1749-1752 (1990).
Schmiegel, Jürgen, and Grützmacher, Hans-Friedrich. “A macrocyclic 2,19-dioxo[3.3](3,3´) azobenzolophane by transition-metal carbonyl complex-mediated CO insertion and cyclization”. Chemische Berichte 123.8 (1990): 1749-1752.
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