Science of Synthesis

Koo, S., Science of Synthesis, (2010) 45, 1403.

Electron-deficient 1-cyclopropylideneacetone undergoes [3 + 2 + 2] cycloaddition with two molecules of phenylacetylene (a bulky terminal alkyne) in the presence of 10 mol% bis(triphenylphosphine)nickel(0), which can be generated in situ from bis(cycloocta-1,5-diene)nickel(0) and triphenylphosphine (‌Scheme 42‌).[‌185‌] Cycloheptatriene ‌190‌ can be obtained in 65% yield after the isomerization of the initially formed cycloheptadiene. This reaction proceeds less effectively with internal alkynes or sterically less congested terminal alkynes, and does not proceed with alkylidenecyclopropanes. The highest yield can be obtained upon slow addition (5 h) of a solution of 1-cyclopropylideneacetone and phenylacetylene to a solution of the nickel catalyst in toluene.

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References

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• 8.Meeeee-Meee, (8888) M 88e, 888.