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Novel five- to ten-membered organoselenium heterocycles from the selenation of aromatic diols

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Date
05/2010
Author
Hua, Guoxiong
Fuller, Amy
Slawin, Alexandra M. Z.
Woollins, J Derek
Keywords
Main group elements
Heterocycles
Phosphorus
Selenium
Organoselenium compounds
P-SE heterocycles
Ray crystal-structures
Woollins reagent
Reactivity
(PHP(SE)(MU-SE))(2)
Cyanamides
Anhydride
Compplexes
QD Chemistry
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Abstract
Reaction of Woollins' reagent ― WR , 2,4-bis(phenyl)-1,3-diselenadiphosphetane 2,4-diselenide [{PhP(Se)(μ-Se)}2] ― with aromatic diols in refluxing toluene afforded a series of novel five- to ten-membered phosphorus-selenium heterocycles 1 – 10 with an O–P(Se)–O or O–P(Se)–Se–P(Se)–O or O–P(Se)–O–P(Se)–O linkage in 12–74 % isolated yields. It was found that the diphosphorus species O–P(Se)–Se–P(Se)–O rings could be readily reduced into the monophosphorus species O–P(Se)–O rings in almost quantitative yields via further reaction with another equivalent of corresponding aromatic diol. All new compounds have been characterized by IR, 1H NMR, 13C NMR, 31P NMR, 77Se NMR, mass spectrometry and elemental analysis or accurate mass measurement. Seven representative X-ray structures are reported.
Citation
Hua , G , Fuller , A , Slawin , A M Z & Woollins , J D 2010 , ' Novel five- to ten-membered organoselenium heterocycles from the selenation of aromatic diols ' , European Journal of Organic Chemistry , vol. 2010 , no. 13 , pp. 2607-2615 . https://doi.org/10.1002/ejoc.201000075
Publication
European Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1002/ejoc.201000075
ISSN
1434-193X
Type
Journal article
Rights
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://dx.doi.org/10.1002/ejoc.201000075
Description
This work is funded by the EPSRC UK
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/8028

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