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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.
Haruki Okawa,; Motoyoshi Sekiya,; Junichiro Osawa,; Tatsuo Wada,; Akira Yamada,; Hiroyuki Sasabe,; Toshiyuki Uryu. A Nonlinear Optical Waveguide of Poly(1,9-decadiyne). Polymer Journal. 1991, 23 147-153.
Christophe Feuvrie,; Jérôme Blanchet,; Martine Bonin,; Laurent Micouin. Synthesis and Reactivity of Mixed Alkynylalanes by Direct Triethylamine-Catalyzed Alumination of Terminal Alkyne. Org. Lett.,. 2004 , 6(14),2333-2336.
Hazard Statements: H226
Flammable liquid and vapour.
Precautionary Statements: P210-P280a-P240-P241-P303+P361+P353-P501a
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