[reaction: see text] Commercially available 1-bromobenzocyclobutene is a potentially useful synthon particularly with the application of organometallic methodology. Here we show that it is readily converted into Cp(2)Zr(benzocyclobutadiene), which couples with alkynes or nitriles giving five-membered zirconacycles. Treatment of these alkyne- or nitrile-derived zirconacycles with CuCl yields substituted naphthalenes, isoquinolines, or in the presence of MeO(2)C-CC-CO(2)Me, a 3-benzazocine containing an eight-membered ring [corrected].
Four isomers of 5,7-dodecadien-l-ol were previously proposed as being the sex pheromone of the pine moth. The isomers were stereoselectively synthesized from 1-hexyne and tetrahydropyranyl ether of 5-hexyn-l-ol.The (5Z, 7Z)-isomer was synthesized by a Chodkiewic Cadiot reaction followed by hydroboration, and other three isomers by novel synthetic methods including the addition of zirconocene hydride [Schwarz's reagent (C5H5)2Zn(H)Cl] to control the regioselective coupling reaction. The 5,8-and 5,9-dodecadien-l-ols were also synthesized by similar methods for comparison of their characteristics with the endogenoussex pheromone.
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