Science of Synthesis

de Meijere, A.; Kozhushkov, S. I., Science of Synthesis, (2009) 48, 572.

The theoretically interesting (CH)12 hydrocarbon [D3d]-octahedrane (‌299‌) had previously been prepared by a multistep synthetic route in 0.6–1.2% overall yield.[‌433‌,‌434‌] A reported intramolecular photochemical criss-cross cycloaddition between two benzene fragments incorporated in the 2,11-diaza[3.3]paracyclophane ‌300‌ [X = NC(O)CF3] leads to the formation of the doubly ring-annulated octahedrane derivative ‌301‌ in one step in 22% yield (33% based on consumed ‌300‌) (‌Scheme 94‌).[‌435‌] Unfortunately, the carbocyclic [3.3]paracyclophane ‌300‌ (X = CH2) does not undergo this photochemical isomerization, and no attempts to transform ‌301‌ into ‌299‌ have been undertaken.

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References

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• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) 88/8, 88.
• 8.Meeeee-Meee, (8888) 88/8, 88.
• 8.Meeeee-Meee, (8888) 88/8, 88.