Ammonium Phenylphosphonamidodiselenoates and Phenylphosphonamidodi-selenoic Diamides from the Selenation of Primary and Secondary Amines

Guoxiong Hua; Rebecca A. M. Randall; Alexandra M. Z. Slawin; J. Derek Woollins

doi:10.1002/zaac.201100257

Ammonium Phenylphosphonamidodiselenoates and Phenylphosphonamidodi-selenoic Diamides from the Selenation of Primary and Secondary Amines

Guoxiong Hua, Rebecca A. M. Randall, Alexandra M. Z. Slawin, J. Derek Woollins

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

Abstract

By reacting two equivalents of primary or secondary amines with 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) at room temperature a series of new ammonium phenylphosphonamidodiselenoates 1-7 have been obtained in good to excellent yields (70-99 %). The first metal complex of phenylphosphonamidodiselenoate, the complex of Cd2L4 (L = [Se2PPh(NCH(CH3)(2)](-)) (8) has been prepared from the reaction of diisopropylamine N-isopropyl-P-phenylphosphonamidodiselenoate with Cd(CH3COO)(2) in dichloromethane. Upon heating to 130 degrees C the ammonium phenylphosphonamidodiselenoates lose hydrogen selenide leading to the corresponding phenylphosphonamidodiselenoic diamides 9-11 in almost quantitative yields. The same products 9-11 can also be prepared directly from the reaction of primary amines with Woollins' reagent in refluxing toluene. Three representative X-ray structures are described.

Original language	English
Pages (from-to)	1800-1806
Number of pages	7
Journal	Zeitschrift für Anorganische und Allgemeine Chemie
Volume	637
Issue number	12
Early online date	25 Aug 2011
DOIs	https://doi.org/10.1002/zaac.201100257
Publication status	Published - Oct 2011

Keywords

Woollins' reagent
Amines
Ammonium phenylphosphonamidodiselenoates
Phenylphosphonamidodiselenoic diamides
X-ray diffraction
Phosphor-1,1-dithiolato metal-complexes
Supramolecular associations
Coordination chemistry
Stereochemical aspects
Molecular-structures
Organic-synthesis
Selenium
Organoselenium
Patterns

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10.1002/zaac.201100257

hua2011zaac1800
© 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an Accepted Manuscript of an article published in Zeitschrift für anorganische und allgemeine Chemie on 25 August 2011, available online: http://onlinelibrary.wiley.com/doi/10.1002/zaac.201100257/pdf
Accepted author manuscript, 564 KB

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title = "Ammonium Phenylphosphonamidodiselenoates and Phenylphosphonamidodi-selenoic Diamides from the Selenation of Primary and Secondary Amines",

abstract = "By reacting two equivalents of primary or secondary amines with 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) at room temperature a series of new ammonium phenylphosphonamidodiselenoates 1-7 have been obtained in good to excellent yields (70-99 %). The first metal complex of phenylphosphonamidodiselenoate, the complex of Cd2L4 (L = [Se2PPh(NCH(CH3)(2)](-)) (8) has been prepared from the reaction of diisopropylamine N-isopropyl-P-phenylphosphonamidodiselenoate with Cd(CH3COO)(2) in dichloromethane. Upon heating to 130 degrees C the ammonium phenylphosphonamidodiselenoates lose hydrogen selenide leading to the corresponding phenylphosphonamidodiselenoic diamides 9-11 in almost quantitative yields. The same products 9-11 can also be prepared directly from the reaction of primary amines with Woollins' reagent in refluxing toluene. Three representative X-ray structures are described.",

keywords = "Woollins' reagent, Amines, Ammonium phenylphosphonamidodiselenoates, Phenylphosphonamidodiselenoic diamides, X-ray diffraction, Phosphor-1,1-dithiolato metal-complexes, Supramolecular associations, Coordination chemistry, Stereochemical aspects, Molecular-structures, Organic-synthesis, Selenium, Organoselenium, Patterns",

author = "Guoxiong Hua and Randall, {Rebecca A. M.} and Slawin, {Alexandra M. Z.} and Woollins, {J. Derek}",

note = "The authors are thankful to the University of St Andrews and the Engineering and Physical Science Research Council (EPSRC, U.K.) for financial support.",

year = "2011",

month = oct,

doi = "10.1002/zaac.201100257",

language = "English",

volume = "637",

pages = "1800--1806",

journal = "Zeitschrift f{\"u}r Anorganische und Allgemeine Chemie",

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publisher = "Wiley-VCH, Weinheim",

number = "12",

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Ammonium Phenylphosphonamidodiselenoates and Phenylphosphonamidodi-selenoic Diamides from the Selenation of Primary and Secondary Amines. / Hua, Guoxiong; Randall, Rebecca A. M.; Slawin, Alexandra M. Z. et al.
In: Zeitschrift für Anorganische und Allgemeine Chemie, Vol. 637, No. 12, 10.2011, p. 1800-1806.

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

TY - JOUR

T1 - Ammonium Phenylphosphonamidodiselenoates and Phenylphosphonamidodi-selenoic Diamides from the Selenation of Primary and Secondary Amines

AU - Hua, Guoxiong

AU - Randall, Rebecca A. M.

AU - Slawin, Alexandra M. Z.

AU - Woollins, J. Derek

N1 - The authors are thankful to the University of St Andrews and the Engineering and Physical Science Research Council (EPSRC, U.K.) for financial support.

PY - 2011/10

Y1 - 2011/10

N2 - By reacting two equivalents of primary or secondary amines with 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) at room temperature a series of new ammonium phenylphosphonamidodiselenoates 1-7 have been obtained in good to excellent yields (70-99 %). The first metal complex of phenylphosphonamidodiselenoate, the complex of Cd2L4 (L = [Se2PPh(NCH(CH3)(2)](-)) (8) has been prepared from the reaction of diisopropylamine N-isopropyl-P-phenylphosphonamidodiselenoate with Cd(CH3COO)(2) in dichloromethane. Upon heating to 130 degrees C the ammonium phenylphosphonamidodiselenoates lose hydrogen selenide leading to the corresponding phenylphosphonamidodiselenoic diamides 9-11 in almost quantitative yields. The same products 9-11 can also be prepared directly from the reaction of primary amines with Woollins' reagent in refluxing toluene. Three representative X-ray structures are described.

AB - By reacting two equivalents of primary or secondary amines with 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) at room temperature a series of new ammonium phenylphosphonamidodiselenoates 1-7 have been obtained in good to excellent yields (70-99 %). The first metal complex of phenylphosphonamidodiselenoate, the complex of Cd2L4 (L = [Se2PPh(NCH(CH3)(2)](-)) (8) has been prepared from the reaction of diisopropylamine N-isopropyl-P-phenylphosphonamidodiselenoate with Cd(CH3COO)(2) in dichloromethane. Upon heating to 130 degrees C the ammonium phenylphosphonamidodiselenoates lose hydrogen selenide leading to the corresponding phenylphosphonamidodiselenoic diamides 9-11 in almost quantitative yields. The same products 9-11 can also be prepared directly from the reaction of primary amines with Woollins' reagent in refluxing toluene. Three representative X-ray structures are described.

KW - Woollins' reagent

KW - Amines

KW - Ammonium phenylphosphonamidodiselenoates

KW - Phenylphosphonamidodiselenoic diamides

KW - X-ray diffraction

KW - Phosphor-1,1-dithiolato metal-complexes

KW - Supramolecular associations

KW - Coordination chemistry

KW - Stereochemical aspects

KW - Molecular-structures

KW - Organic-synthesis

KW - Selenium

KW - Organoselenium

KW - Patterns

U2 - 10.1002/zaac.201100257

DO - 10.1002/zaac.201100257

M3 - Article

SN - 0044-2313

VL - 637

SP - 1800

EP - 1806

JO - Zeitschrift für Anorganische und Allgemeine Chemie

JF - Zeitschrift für Anorganische und Allgemeine Chemie

IS - 12

ER -

Ammonium Phenylphosphonamidodiselenoates and Phenylphosphonamidodi-selenoic Diamides from the Selenation of Primary and Secondary Amines

Abstract

Keywords

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