Novel five- and six-membered ring phosphorus-selenium heterocycles from selenation of amido-Schiff bases
Abstract
Woollins’ reagent, [2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide], serving as a selenating-reductive cycloaddition reagent, reacts with nonconjugated amido-Schiff bases to give the corresponding six-membered 1,3,4-selenadiazoles via a ring-expansion accompanied by an additional selenation/cyclization to the imine bond and C═O group; meanwhile, under the same reaction conditions, the selenation of conjugated amido-Schiff bases leads to a series of fused heterocycles with two five-membered rings. Eight single-crystal X-ray structures confirming the formation of these five- and six-membered heterocycles are discussed.
Citation
Hua , G , Cordes , D B , Slawin , A M Z & Woollins , J D 2020 , ' Novel five- and six-membered ring phosphorus-selenium heterocycles from selenation of amido-Schiff bases ' , ACS Omega , vol. 5 , no. 20 , pp. 11737-11744 . https://doi.org/10.1021/acsomega.0c01064
Publication
ACS Omega
Status
Peer reviewed
ISSN
2470-1343Type
Journal article
Rights
Copyright © 2020 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Description
Authors are grateful to the University of St Andrews for financial support.Collections
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