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Organophosphorus-Selenium Heteroatom Derivatives from Selenation of Primary/Secondary Amines and Haloalkanes/Dihaloalkanes

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Date
11/2013
Author
Hua, Guoxiong
Arachchige, Kasun S. A.
Slawin, Alexandra M. Z.
Woollins, J. Derek
Keywords
Woollins' reagent
Selenium
Phosphorus
Amines
Haloalkanes
Crystal structures
QD Chemistry
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Abstract
Reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) with four equivalents of primary/secondary amines led to a series of ammonium phenylphosphonamido-diselenoates or phenylphosphonamido-diselenoic diamides 1a-n, the latter further reacted in situ with either two equivalents of haloalkanes or an equimolar amount of dihaloalkane, resulting in formation of the corresponding Se-alkylphenyl-Se-alkylphenyl-phosphonamidodiselenoates 2a-n and alkane bis(N-alkyl-P-phenylphosphonamido-diselenoate) derivatives 3a-n in good to excellent yields. All new compounds have been characterized spectroscopically including multinuclear NMR (H-1, C-13, P-31 and Se-77), IR and mass spectroscopy. Two representative X-ray structures are also described.
Citation
Hua , G , Arachchige , K S A , Slawin , A M Z & Woollins , J D 2013 , ' Organophosphorus-Selenium Heteroatom Derivatives from Selenation of Primary/Secondary Amines and Haloalkanes/Dihaloalkanes ' , European Journal of Organic Chemistry , vol. 2013 , no. 32 , pp. 7402-7410 . https://doi.org/10.1002/ejoc.201300860
Publication
European Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1002/ejoc.201300860
ISSN
1434-193X
Type
Journal article
Rights
Copyright 2013, Wiley. This is the accepted version of the following article: Guoxiong, H. et al (2013). ‘Organophosphorus-Selenium Heteroatom Derivatives from Selenation of Primary/Secondary Amines and Haloalkanes/Dihaloalkanes’, European Journal of Organic Chemistry, Vol 2013 (32) pp. 7402–7410, which has been published in final form at: DOI: 10.1002/ejoc.201300860
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/5492

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