Synthesis of novel 2,5-diarylselenophenes from selenation of 1,4-diarylbutane-1,4-diones or methanol/arylacetylenes
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Reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide [PhP(Se)(mu-Se)](2) (Woollins' reagent, WR) with one equivalent of 1,4-diarylbutane-1,4-diones 1a-g in refluxing toluene affords the corresponding 2,5-diarylselenophenes 2a-g in excellent yields (up to 99%). Alternatively, the 2,5-diarylselenophenes (2a and 2b) can be obtained in 70-80% yields from the reaction of arylacetylene with an equivalent of O-methyl Se-hydrogen phenylphosphonodiselenoate; the latter was derived from WR and methanol. The first X-ray structure of 2,5-diarylselenophenes is presented along with characterisation of their redox properties.
Hua , G , Henry , J B , Li , Y , Mount , A R , Slawin , A M Z & Woollins , J D 2010 , ' Synthesis of novel 2,5-diarylselenophenes from selenation of 1,4-diarylbutane-1,4-diones or methanol/arylacetylenes ' Organic & Biomolecular Chemistry , vol 8 , no. 7 , pp. 1655-1660 . DOI: 10.1039/b924986a
Organic & Biomolecular Chemistry
This is the author's version of an article in Organic and Biomolecular Chemistry. The published version (c)Royal Society of Chemistry is available from DOI: 10.1039/B924986A
This work is funded by the EPSRC UK
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