Synthesis 2013; 45(2): 199-204
DOI: 10.1055/s-0032-1316830
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1-Amino-2,5-dihydro-1H-phosphole 1-Oxides and Their N-Phosphinoyl Derivatives, Bis(2,5-dihydro-1H-phosphol-1-yl)amine P,P′-Dioxides

Nóra Zsuzsa Kiss
a   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp.3, 1521 Budapest, Hungary
,
András Simon
b   Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Műegyetem rkp.3, 1521 Budapest, Hungary
,
László Drahos
c   Hungarian Academy of Sciences, Chemical Research Center, Pusztaszeri út 59-67, 1525 Budapest, Hungary
,
Krzysztof Huben
d   Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Łódź, Poland   Fax: +36(1)4633648   Email: gkeglevich@mail.bme.hu
,
Stefan Jankowski
d   Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Łódź, Poland   Fax: +36(1)4633648   Email: gkeglevich@mail.bme.hu
,
György Keglevich*
a   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp.3, 1521 Budapest, Hungary
› Author Affiliations
Further Information

Publication History

Received: 29 October 2012

Accepted after revision: 29 November 2012

Publication Date:
12 December 2012 (online)


Abstract

Depending on the molar ratio of the reactants and on the order of mixing, the reactions of a series of primary amines with 1-chloro-2,5-dihydro-1H-phosphole 1-oxides prepared in situ from the corresponding hydroxy-dihydrophosphole oxides afforded 1-amino-2,5-dihydro-1H-phosphole 1-oxides, or their N-phosphinoyl derivatives, bis(2,5-dihydro-1H-phosphol-1-yl)amine P,P′-dioxides. The latter family of P-heterocycles could also be synthesized by the reaction of 1-amino-2,5-dihydro-1H-phosphole oxides with chloro-dihydrophosphole oxides.

 
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