Synthesis and structural study of novel selenation derivatives of N, N-Dialkylcyanamides
Abstract
The reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide {[PhP(Se)(µ-Se)]2, Woollins’ reagent, WR } with N, N-dialkylcyanamides 1–3 in refluxing toluene solution led to the corresponding [2+3] cycloaddition products 4-dialkylamino-2,5-diphenyl-1,3,2,5-selenazadiphosphole 2,5-diselenides 4–6 in good yields, the latter were further treated with water resulting in the corresponding hydrolysis derivatives dialkyl-selenoureas 7–9 , and phosphinodiselenoates 10 and 11 . Selenourea 7 could be transferred into 1,3-selenazol-2-amines 12–15 in excellent yields by further cyclization with four different α-haloketones. All new compounds have been characterized by IR spectroscopy, multi-NMR (1H, 13C, 31P, 77Se) spectroscopy and accurate mass measurement. The single crystal X-ray structural features of nine new compounds are also discussed.
Citation
Hua , G , Du , J , Slawin , A M Z & Woollins , J D 2016 , ' Synthesis and structural study of novel selenation derivatives of N, N -Dialkylcyanamides ' , ChemistrySelect , vol. 1 , no. 21 , pp. 6810-6817 . https://doi.org/10.1002/slct.201601577
Publication
ChemistrySelect
Status
Peer reviewed
ISSN
2365-6549Type
Journal article
Description
We are grateful to the University of St Andrews for financial support and the EPSRC National Mass Spectrometry Service Centre (Swansea) for mass spectral measurements.Collections
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