Novel organo phosphorus-selenium heteroatom compounds from selenation of diamines

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

doi:10.1016/j.tet.2013.04.135

Novel organo phosphorus-selenium heteroatom compounds from selenation of diamines

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	5299-5305
Number of pages	7
Journal	Tetrahedron
Volume	69
Issue number	26
Early online date	7 May 2013
DOIs	https://doi.org/10.1016/j.tet.2013.04.135
Publication status	Published - 1 Jul 2013

Keywords

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

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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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title = "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.",

keywords = "Diamines, Selenides, Woollins' reagent, o-Xylylenedibromide, P-Se heteroatom compounds, Single crystal X-ray structures",

author = "Guoxiong Hua and Randall, \{Rebecca Amy Michele\} and Slawin, \{Alexandra Martha Zoya\} and Woollins, \{J Derek\}",

year = "2013",

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doi = "10.1016/j.tet.2013.04.135",

language = "English",

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T1 - Novel organo phosphorus-selenium heteroatom compounds from selenation of diamines

AU - Hua, Guoxiong

AU - Randall, Rebecca Amy Michele

AU - Slawin, Alexandra Martha Zoya

AU - Woollins, J Derek

PY - 2013/7/1

Y1 - 2013/7/1

N2 - 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.

AB - 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.

KW - Diamines

KW - Selenides

KW - Woollins' reagent

KW - o-Xylylenedibromide

KW - P-Se heteroatom compounds

KW - Single crystal X-ray structures

UR - https://www.scopus.com/pages/publications/84878233661

U2 - 10.1016/j.tet.2013.04.135

DO - 10.1016/j.tet.2013.04.135

M3 - Article

SN - 0040-4020

VL - 69

SP - 5299

EP - 5305

JO - Tetrahedron

JF - Tetrahedron

IS - 26

ER -

Novel organo phosphorus-selenium heteroatom compounds from selenation of diamines

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Keywords

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