Novel organo phosphorus-selenium heteroatom compounds from selenation of diamines
Abstract
Reaction of Woollins' reagent (WR) with trans-1,2-cyclohexanediamine or 1,3-cyclohexanediamine, followed by treatment with o-xylylenedibromide in THF at room temperature surprisingly led to 3-phenyl-1,5-dihydrobenzo[e][1,3,2]diselenaphosphepine 3-selenide (3). However, using o-phenylenediamine, the same product together with 1,4-dihydrobenzo[d][1,2]diselenine (9) was obtained. Furthermore, treating WR with N,N'-dibenzylethane-1,2-diamine gave rise to 1,3-dibenzyl-2-phenyl-1,3,2-diazaphospholidine 2-selenide (10) and a zwitterionic product N-benzyl-N-(2-(benzylammonio)ethyl)-P-phenylphosphonamidodiselenoate (11). Unexpectedly, WR reacted with 2,2'-disulfanediyldianiline under identical conditions affording the known product: 2-phenyl-2,3-dihydrobenzo[d][1,3,2]thiazaphosphole 2-selenide (13). Three representative X-ray structures are reported. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.
Citation
Hua , G , Randall , R A M , Slawin , A M Z & Woollins , J D 2013 , ' Novel organo phosphorus-selenium heteroatom compounds from selenation of diamines ' , Tetrahedron , vol. 69 , no. 26 , pp. 5299-5305 . https://doi.org/10.1016/j.tet.2013.04.135
Publication
Tetrahedron
Status
Peer reviewed
ISSN
0040-4020Type
Journal article
Rights
Copyright 2013, Elsevier. NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, Vol 69 (26) 2013. DOI: http://dx.doi.org/10.1016/j.tet.2013.04.135
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