Generation and Cycloaddition of o-Quinodimethane in Aqueous Medium

doi:10.3390/60500472

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

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Generation and Cycloaddition of o-Quinodimethane in Aqueous Medium

Lothar W. Bieber* and Margarete F. Da Silva

Departamento de Química Fundamental, Universidade Federal de Pernambuco, Cidade Universitária, 50670-901 Recife - PE, Brazil

* Author to whom correspondence should be addressed.

Received: 9 March 2001; in revised form: 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

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MDPI and ACS Style

Bieber, L.W.; Da Silva, M.F. Generation and Cycloaddition of o-Quinodimethane in Aqueous Medium. Molecules 2001, 6, 472-476.

AMA Style

Bieber LW, Da Silva MF. Generation and Cycloaddition of o-Quinodimethane in Aqueous Medium. Molecules. 2001; 6(5):472-476.

Chicago/Turabian Style

Bieber, Lothar W.; Da Silva, Margarete F. 2001. "Generation and Cycloaddition of o-Quinodimethane in Aqueous Medium." Molecules 6, no. 5: 472-476.

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