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Generation and Cycloaddition of o-Quinodimethane in Aqueous Medium
Departamento de Química Fundamental, Universidade Federal de Pernambuco, Cidade Universitária, 50670-901 Recife - PE, Brazil
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Received: 9 March 2001; in revised form: 24 April 2001 / Accepted: 24 March 2001 / Published: 30 April 2001
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
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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.
Bieber LW, Da Silva MF. Generation and Cycloaddition of o-Quinodimethane in Aqueous Medium. Molecules. 2001; 6(5):472-476.
Bieber, Lothar W.; Da Silva, Margarete F. 2001. "Generation and Cycloaddition of o-Quinodimethane in Aqueous Medium." Molecules 6, no. 5: 472-476.