Demystifying the dendralenes*
نویسندگان
چکیده
We present herein an overview of our ongoing studies with dendralenes. The first synthetic routes to this fundamental family of compounds have revealed long-hidden secrets in hydrocarbon chemistry and set the scene for synthetic and materials chemistry applications.
منابع مشابه
Synthesis of substituted [3]dendralenes and their unique cycloaddition reactions.
Dimethylsulfonium methylide mediated olefination of 2-phenylethenylidene phosphonoacetate followed by the Horner-Wadsworth-Emmons reaction with aromatic aldehydes provided access to reactive 1,5-diaryl-2-ethoxycarbonyl [3]dendralenes which in situ underwent Diels-Alder cyclodimerisation leading to highly functionalised cyclohexenes with very high regio- and stereoselectivity.
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Selective elimination from 1,3-dienic allylic carbonates occurs in the presence of a catalytic amount of [Ru(C(5)Me(5))(4,4'-di-Bu(t)-2,2'-bipyridine)(CH(3)CN)]PF(6) and provides efficient access to a variety of [3]dendralenes.
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The synthesis of two [4]-dendralene compounds incorporating thiophene-(p-nitrophenyl) donor-acceptor units is presented. The dendralenes adopt two different conformers in solution and solid state and the transformation between the structures can be controlled by light and heat. The electron-donating components of the dendralenes are represented by bromothienyl (in 13) and ethylenedioxythiophene...
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The first general synthesis of 1-substituted [3]dendralenes has led to the discovery that conjugating groups significantly enhance the rate of Diels-Alder dimerisation relative to both the parent [3]dendralene and to other substituted systems.
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