Novel organo phosphorus-selenium heteroatom compounds from selenation of diamines

Guoxiong Hua, Rebecca Amy Michele Randall, Alexandra Martha Zoya Slawin, J Derek Woollins

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8 Citations (Scopus)
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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.

Original languageEnglish
Pages (from-to)5299-5305
Number of pages7
JournalTetrahedron
Volume69
Issue number26
Early online date7 May 2013
DOIs
Publication statusPublished - 1 Jul 2013

Keywords

  • Diamines
  • Selenides
  • Woollins' reagent
  • o-Xylylenedibromide
  • P-Se heteroatom compounds
  • Single crystal X-ray structures

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