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
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