Synthesis of hexaisopropyltriamidephosphite: Myth or reality?

Full text of DOI:10.1080/10426500701808184

This article was downloaded by: [The University of Manchester Library]
On: 13 October 2014, At: 07:59
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Phosphorus, Sulfur, and Silicon
and the Related Elements
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/gpss20
Synthesis of
Hexaisopropyltriamidephosphite:
Myth or Reality?
Anatoliy P. Marchenko a , Georgyi N. Koidan , Yurii
M. Pustovit a , Mark I. Povolotskii a , Aleksandr N.
Chernega a & Aleksandr M. Pinchuk a
a Institute of Organic Chemistry National Academy of
Sciences of Ukraine , Murmanska Str. 5, Kyiv, 02094,
Ukraine
Published online: 20 Jun 2008.
To cite this article: Anatoliy P. Marchenko , Georgyi N. Koidan , Yurii M. Pustovit ,
Mark I. Povolotskii , Aleksandr N. Chernega & Aleksandr M. Pinchuk (2008) Synthesis of
Hexaisopropyltriamidephosphite: Myth or Reality?, Phosphorus, Sulfur, and Silicon and
the Related Elements, 183:2-3, 797-798, DOI: 10.1080/10426500701808184
To link to this article: http://dx.doi.org/10.1080/10426500701808184
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the
information (the “Content”) contained in the publications on our platform.
However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness,
or suitability for any purpose of the Content. Any opinions and views
expressed in this publication are the opinions and views of the authors, and
are not the views of or endorsed by Taylor & Francis. The accuracy of the
Content should not be relied upon and should be independently verified with
primary sources of information. Taylor and Francis shall not be liable for any
losses, actions, claims, proceedings, demands, costs, expenses, damages,

and other liabilities whatsoever or howsoever caused arising directly or
indirectly in connection with, in relation to or arising out of the use of the
Content.
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden. Terms & Conditions of access and use can be found at
http://www.tandfonline.com/page/terms-and-conditions

Phosphorus, Sulfur, and Silicon, 183:797–798, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500701808184
Synthesis of Hexaisopropyltriamidephosphite:
Myth or Reality?
Anatoliy P. Marchenko, Georgyi N. Koidan,
Yurii M. Pustovit, Mark I. Povolotskii,
Aleksandr N. Chernega, and Aleksandr M. Pinchuk
Institute of Organic Chemistry National Academy of Sciences
of Ukraine, Murmanska Str. 5, Kyiv, 02094 Ukraine
Results of our work allowed us to assert that the methods for synthe-
sis of triamide (i-Pr2N)3P 1 described are wrong.1–4 It was shown that
diamidohalogenphosphites (i-Pr2N)2PHlg (Hlg = Cl,Br,I) do not react
with di(isopropyl)amine even under harsh conditions such as heating
up to 240◦C in various solvents. At the same time, less sterically hin-
dered phosphenium cation 2 easily react with di(isopropyl)amine, af-
fording diphosphine 5 instead of the expected triamide 1. The diphos-
phine 5 is also formed in the reaction of the phosphenium cation 2 with
ketimine i-PrN = CMe2, with the reaction running via formation of
monophosphine 3.
In conclusion we must note that an approach to triamide 1 has to be
found yet.
Address correspondence to Georgyi N. Koidan, Institute of Organic Chemistry Na-
tional Academy of Sciences of Ukraine, Murmanska Str.5, Kyiv, 02094 Ukraine.
797

798
A. P. Marchenko et al.
REFERENCES
[1] A. Michaelis, Lieb. Ann., 326, 129 (1903).
[2] E. E. Nifantyev, S. V. Suvorkin, and E. N. Rasadkina, Zhur. Obshch. Khimii, 72, 1263
(2002).
[3] H. Hund, R.-D. Hund, S. Has, et al., Phosphorus, Sulfur and Silicon, 111, P. 193
(1996).
[4] A. D. Sinitsa, et al., Zhur. Obshch. Khimii, 67, 67 (1997).