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1,2-Disubstituted cyclopropene, 1-methyl-2-phenylcyclopropene (18), was generated by bromo-lithium exchange of 1-bromo-2-phenylcyclopropene followed by treatment with methyl iodide. Compound 18 was oxidized by oxygen to give the α,β-unsaturated carbonyl product 25 and diketone 27 and the tautomeric, β-hydroxyl-α,β-unsaturated ketone 28. However, compound 28 reacted further with the cyclopropene 18...
The 1,3‐fused polycyclic cyclopropene, tricyclo[3.2.1.02,4]oct‐2(3)‐ene 25, was synthesized by the elimination of trimethylsilyl chloride from 2‐chloro‐3‐(trimethylsilyl)tricyclo[3.2.1.02,4]octane 20. However, the high strain in the system favors the ring‐opened vinylcarbene form, which undergoes a number of reactions including the addition of water, insertion into the C–H bond α to the oxygen atom...
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