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Synthesis 2010(14): 2437-2445  
DOI: 10.1055/s-0029-1218817
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Preparation of Dialkyl 1-(Alkylamino)alkylphosphonates, Alkyl [1-(Alkylamino)alkyl]phenylphosphinates and [1-(Alkylamino)alkyl]di­phenylphosphine Oxides via ‘In Situ’ Generated Iminium Ions

Waldemar Goldeman, Mirosaw Soroka*
Politechnika Wrocawska, Department of Chemistry, Wybrzeże Wyspiańskiego 27, 50370 Wrocaw, Poland
Fax: +48(71)3284064; e-Mail: miroslaw.soroka@pwr.wroc.pl;
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Publication History

Received 27 January 2010
Publication Date:
15 June 2010 (online)

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Abstract

The reaction of trialkyl phosphites, dialkyl phenylphosphonites or alkyl diphenylphosphinites with N-alkylalkanimines in the presence of hydrogen chloride gives dialkyl 1-(alkylamino)alkylphosphonates, alkyl [1-(alkylamino)alkyl]phenylphosphinates or [1-(alkylamino)alkyl]diphenylphosphine oxides respectively, via Arbusov-like reaction of iminium salts generated ‘in situ’ from N-alkylalkanimines. This reaction is an alternative and competitive to known method of preparation based on the addition of H-P compounds to N-alkylalkanimines, because it gives higher yields, no heating is necessary, and the isolation of products is easy.

Key words

aminophosphonates - aminophosphinates - imines - Schiff bases - nucleophilic addition

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