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Molecules 2001, 6(5), 472-476; doi:10.3390/60500472
Article

Generation and Cycloaddition of o-Quinodimethane in Aqueous Medium

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Received: 9 March 2001 / Revised: 24 April 2001 / Accepted: 24 March 2001 / Published: 30 April 2001
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Abstract

o-Quinodimethane can be generated from =α,α'-dihalo-o-xylenes using zinc in aqueous solution. In the presence of activated dienophiles cycloadducts can be obtained directly. Catalysis with tris-triphenylphosphine ruthenium(II) dichloride reduces side reactions such as reduction and polymerisation and improves the yield. This is the first example of an organometallic cyclisation in aqueous medium using dihalo compounds.
Keywords: Dehalogenation; zinc; Diels-Alder reaction; Ru catalysis; aqueous solvent Dehalogenation; zinc; Diels-Alder reaction; Ru catalysis; aqueous solvent
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Bieber, L.W.; Da Silva, M.F. Generation and Cycloaddition of o-Quinodimethane in Aqueous Medium. Molecules 2001, 6, 472-476.

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