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1,6-Dichlorohexa-2,4-diyne undergoes nickel-catalyzed double substitution with aryl and alkenyl Grignard reagents to provide substituted ene-yne-enes. The reaction is formally an extension of the well-described S(N)2 '-allylic and -propargylic substitution reactions but the mechanism is considerably more complex. The products might function as building blocks for conjugated polymers

Synthesis of ene-yne-enes by nickel-catalyzed double SN2′ substitution of 1,6-dichlorohexa-2,4-diyne

Synthesis of ene-yne-enes by nickel-catalyzed double S_N2′ substitution of 1,6-dichlorohexa-2,4-diyne