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Issue 8, 2010
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Reactions of germenes with various naphthoquinones controlled by substituent effects

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Abstract

The germene Mes2Ge[double bond, length as m-dash]CR21 (Mes = 2,4,6-trimethylphenyl, CR2 = fluorenylidene) reacts with 5-methoxy-1,4-naphthoquinone to yield, via the o-quinodimethane 8, the endoperoxyde 9 by simple reaction with molecular oxygen. By contrast, 1 with 2,3-dichloro-1,4-naphthoquinone gives the tetracyclic compound 7 by a double [2 + 4] cycloaddition between the Ge[double bond, length as m-dash]C double bond and the conjugated system O[double bond, length as m-dash]C–CH[double bond, length as m-dash]CH. The new steric demanding germene Mes2Ge[double bond, length as m-dash]CR′25 (CR′2 = 2,7-di-tert-butylfluorenylidene) undergoes similar [2 + 4] cycloadditions with various substituted or unsubstituted naphthoquinones, leading to tetracyclic adducts 10–12. The germene 5, the endoperoxide 9 and the cycloadducts 10 and 12 have been structurally characterized.

Graphical abstract: Reactions of germenes with various naphthoquinones controlled by substituent effects

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Publication details

The article was received on 16 Oct 2009, accepted on 18 Nov 2009 and first published on 12 Jan 2010


Article type: Paper
DOI: 10.1039/B921729K
Citation: Dalton Trans., 2010,39, 2016-2022
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    Reactions of germenes with various naphthoquinones controlled by substituent effects

    D. Ghereg, H. Gornitzka, H. Ranaivonjatovo and J. Escudié, Dalton Trans., 2010, 39, 2016
    DOI: 10.1039/B921729K

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