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Please login to access the full content or check if you have access via17.6.5.2.2.1.1 Variation 1: By Photolysis of 11-Oxatetracyclo[6.5.0.09,13.010,12]trideca-2,4,6-triene and Similar Compounds
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Borzilleri, R. M., Science of Synthesis, (2004) 17, 1018.
Photolysis of 11-oxatetracyclo[6.5.0.09,13.010,12]trideca-2,4,6-triene (186) at −75°C in diethyl ether provides what is believed to be oxa[13]annulene, as a mixture of geometric isomers 187/188, along with 5-oxatricyclo[7.4.0.04,6]tridecatetraene (189) (Scheme 48).[131] Irradiation of the tetracyclic aziridine 190, or the azide 192, at low temperature in diethyl ether or pentane with a low-pressure mercury lamp leads to the aza-annulenes 191 or 193, respectively.[132,133] Both compounds are capable of valence tautomerism, and temperature-dependent NMR spectroscopy shows the dark violet crystalline aza[14]annulene 193 to be planar, extensively delocalized and distinctly diatropic; it is conformationally mobile.[133]
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References
| [131] | Meeee, M.; Meeeee, M.; Meeeöeee, M., Meee. Mee., (8888) 888, 8888. |
| [132] | Meeeöeee, M.; Meeee, M.; Mee, M. M. M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [133] | Möeeeee, M.; Meeeöeee, M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
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