Diene Condensation of Cyclopentadiene with Dienophiles of Allylacetylene Series

Diene condensation of cyclopentadiene with 2-substituted allylacetylenes occurs nonselectively at a double and triple bonds; therewith the dienophile activity grows in parallel with the electron-withdrawing properties of the substituent. Depending on electronic character of functional groups the reaction proceeds as neutral diene synthesis. The relative activity of cyclopentadiene and 1,3-cyclohexadiene in reactions with allylacetylenes is essentially governed by the different distance between the 1,4-reactive sites in these systems.