Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes
AbstractHerein we describe the synthesis of organoselanyl and organotellanyl alkynes by the addition of lithium alkynylchalcogenolate (Se and Te) to tosyl solketal, easily obtained from glycerol. The alkynylchalcogenolate anions were generated in situ and added to tosyl solketal in short reaction times, furnishing in all cases the respective products of substitution in good yields. Some of the prepared compounds were deprotected using an acidic resin to afford new water-soluble 3-organotellanylpropane-1,2-diols. The synthetic versatility of the new chalcogenyl alkynes was demonstrated in the iodocyclization of 2,2-dimethyl-1,3-dioxolanylmethyl(2-methoxyphenylethynyl)selane 3f, which afforded 3-iodo-2-(2,2-dimethyl-1,3-dioxolanylmethyl) selenanylbenzo[b]furan in 85% yield, opening a new way to access water-soluble Se-functionalized benzo[b]furanes. View Full-Text
- Supplementary File 1:
PDF-Document (PDF, 3236 KB)
Share & Cite This Article
Lenardão, E.J.; Borges, E.L.; Stach, G.; Soares, L.K.; Alves, D.; Schumacher, R.F.; Bagnoli, L.; Marini, F.; Perin, G. Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes. Molecules 2017, 22, 391.
Lenardão EJ, Borges EL, Stach G, Soares LK, Alves D, Schumacher RF, Bagnoli L, Marini F, Perin G. Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes. Molecules. 2017; 22(3):391.Chicago/Turabian Style
Lenardão, Eder J.; Borges, Elton L.; Stach, Guilherme; Soares, Liane K.; Alves, Diego; Schumacher, Ricardo F.; Bagnoli, Luana; Marini, Francesca; Perin, Gelson. 2017. "Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes." Molecules 22, no. 3: 391.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.