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Microwave-Assisted Group-Transfer Cyclization of Organotellurium Compounds
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I. Organisk kemi.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
2004 (engelsk)Inngår i: The Journal of Organic Chemistry, Vol. 69, nr 15, s. 5143-5146Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Primary- and secondary-alkyl aryl tellurides, prepared by arenetellurolate ring-opening of epoxides/O-allylation, were, found to undergo rapid (3-10 min) group-transfer cyclization to afford tetrahydrofuran derivatives in 60-74% yield when heated in a microwave cavity at 250C in ethylene glycol or at 180C in water. To go to completion, similar transformations had previously required extended photolysis in refluxing benzene containing a substantial amount of hexabutylditin. The only drawback of the microwave-assisted process was the loss in diastereoselectivity wich is a consequence of the higher reaction temperature. Substitution in the Te-aryl moiety of the secondary-alkyl aryl tellurides (4-OMe, 4-H, 4-CF3) did not affect the outcome of the group-transfer reaction in ethylene glycol. However, at lower temperature, using water as a solvent, the CF3 derivative failed to react. The microwave-assisted grouptransfer cyclization was extended to benzylic but not to primary- and secondary-alkyl phenyl selenides.

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2004. Vol. 69, nr 15, s. 5143-5146
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URN: urn:nbn:se:uu:diva-69538OAI: oai:DiVA.org:uu-69538DiVA, id: diva2:97449
Tilgjengelig fra: 2005-04-05 Laget: 2005-04-05 Sist oppdatert: 2011-01-12

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