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Statements

Subject Item
n2:RIV%2F00216208%3A11310%2F13%3A10141580%21RIV14-MSM-11310___
rdf:type
skos:Concept n15:Vysledek
rdfs:seeAlso
http://dx.doi.org/10.1002/ejoc.201201400
dcterms:description
The synthesis of electron-rich P-1 phosphazene bases with a sterically protected basic center by a Staudinger reaction is reported. The initial products of the reaction between peralkylated triaminophosphanes and bulky alkyl azides, phosphazides 1a-f, were isolated in all cases in good to quantitative yield. The structures of 1d and 1e were confirmed by single-crystal X-ray diffraction. Acidic hydrolysis of pyrrolidino-substituted phosphazide (pyrr)(3)PN(3)tBu 1d led to the quantitative formation of aminophosphonium salt (pyrr)(3)PNH2+center dot BF4- 8, a direct precursor to a Schwesinger's %22building block%22 synthetic unit. Thermally induced denitrogenation of the phosphazides, which is the second step performed in most cases under solvent-free conditions gave P-1 phosphazene bases 2a-f in moderate to excellent yields. A %22one-pot%22 two-step synthesis of phosphazene bases from commercially available triaminophosphanes was discovered. Most of the syntheses were performed on a large laboratory scale. The basicities of the newly synthesized bases 2e and 2f were determined. X-ray crystal structures were obtained for base 2e and for protonated species 2d center dot HBF4, 2e center dot HBF4, and 2f center dot HOTs, which provided the crucial geometrical parameters around the basic center. A rationale for the higher basicity of the pyrrolidino- (pyrr)(3)P=NR than the piperidino- (pip)(3)P=NR phosphazenes is presented. The synthesis of electron-rich P-1 phosphazene bases with a sterically protected basic center by a Staudinger reaction is reported. The initial products of the reaction between peralkylated triaminophosphanes and bulky alkyl azides, phosphazides 1a-f, were isolated in all cases in good to quantitative yield. The structures of 1d and 1e were confirmed by single-crystal X-ray diffraction. Acidic hydrolysis of pyrrolidino-substituted phosphazide (pyrr)(3)PN(3)tBu 1d led to the quantitative formation of aminophosphonium salt (pyrr)(3)PNH2+center dot BF4- 8, a direct precursor to a Schwesinger's %22building block%22 synthetic unit. Thermally induced denitrogenation of the phosphazides, which is the second step performed in most cases under solvent-free conditions gave P-1 phosphazene bases 2a-f in moderate to excellent yields. A %22one-pot%22 two-step synthesis of phosphazene bases from commercially available triaminophosphanes was discovered. Most of the syntheses were performed on a large laboratory scale. The basicities of the newly synthesized bases 2e and 2f were determined. X-ray crystal structures were obtained for base 2e and for protonated species 2d center dot HBF4, 2e center dot HBF4, and 2f center dot HOTs, which provided the crucial geometrical parameters around the basic center. A rationale for the higher basicity of the pyrrolidino- (pyrr)(3)P=NR than the piperidino- (pip)(3)P=NR phosphazenes is presented.
dcterms:title
Synthesis of Electron-Rich Sterically Hindered P-1 Phosphazene Bases by the Staudinger Reaction Synthesis of Electron-Rich Sterically Hindered P-1 Phosphazene Bases by the Staudinger Reaction
skos:prefLabel
Synthesis of Electron-Rich Sterically Hindered P-1 Phosphazene Bases by the Staudinger Reaction Synthesis of Electron-Rich Sterically Hindered P-1 Phosphazene Bases by the Staudinger Reaction
skos:notation
RIV/00216208:11310/13:10141580!RIV14-MSM-11310___
n15:predkladatel
n20:orjk%3A11310
n3:aktivita
n7:Z n7:I
n3:aktivity
I, Z(AV0Z40550506), Z(MSM0021620857)
n3:cisloPeriodika
9
n3:dodaniDat
n9:2014
n3:domaciTvurceVysledku
n8:3157962
n3:druhVysledku
n21:J
n3:duvernostUdaju
n6:S
n3:entitaPredkladatele
n10:predkladatel
n3:idSjednocenehoVysledku
109528
n3:idVysledku
RIV/00216208:11310/13:10141580
n3:jazykVysledku
n17:eng
n3:klicovaSlova
structure-activity relationships; basicity; azides; Staudinger reaction; phosphazides; phosphazenes
n3:klicoveSlovo
n11:structure-activity%20relationships n11:phosphazenes n11:phosphazides n11:azides n11:Staudinger%20reaction n11:basicity
n3:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n3:kontrolniKodProRIV
[8F7D8490FBE6]
n3:nazevZdroje
European Journal of Organic Chemistry
n3:obor
n16:CC
n3:pocetDomacichTvurcuVysledku
1
n3:pocetTvurcuVysledku
7
n3:rokUplatneniVysledku
n9:2013
n3:svazekPeriodika
neuveden
n3:tvurceVysledku
Polyakova, Svetlana M. Alexandrova, Anastasia V. Leito, Ivo Lyapkalo, Ilya M. Saame, Jaan Mašek, Tomáš Císařová, Ivana
n3:wos
000316199300025
n3:zamer
n18:AV0Z40550506 n18:MSM0021620857
s:issn
1434-193X
s:numberOfPages
13
n19:doi
10.1002/ejoc.201201400
n14:organizacniJednotka
11310