One-step synthesis of carbametacyclophane 3 from 1,9-decadiyne and diethyl acetylenedicarboxylate is described. The use of 1,9-decadiyne as a nucleophile led only to the monoalkynylation product, a selectivity that would be difficult to achieve with a catalytic in situ metalation process. 1,9-decadiyne reacts with iodobenzene (excess) to afford the bis-Sonogashira coupling product in excellent yield. 1,9-Decadiyne was dihydrated and gave 2,9-decanedione in 92% yield.

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