Novel organo phosphorus-selenium heteroatom compounds from selenation of diamines

TETRAHEDRON

卷:69

Article

Hua, Guoxiong¹  Randall, Rebecca A. M.¹  Slawin, Alexandra M. Z.¹  Woollins, J. Derek¹ 

[1] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland

关键词: Diamines;    Selenides;    Woollins' reagent;    o-Xylylenedibromide;    P-Se heteroatom compounds;    Single crystal X-ray structures;   

DOI  :  10.1016/j.tet.2013.04.135

来源: Elsevier

【 摘 要 】

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.

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