40561-09-9Relevant academic research and scientific papers
Synthesis, reactivity and stereochemistry of new phosphorus heterocycles with 5- or 6-membered rings
Cristau, Henri-Jean,Pirat, Jean-Luc,Virieux, David,Monbrun, Jér?me,Ciptadi, Ciptadi,Bekro, Yves-Alain
, p. 2472 - 2481 (2007/10/03)
Syntheses of novel phosphorus heterocycles containing α-amino or α-hydroxyphosphonic or phosphinic acids motifs are developed. 2,3-dihydro-1,3-oxaphospholes (1) and 1,4,2-oxazaphosphinanes (2) exhibit a reactive part, respectively the enolether moiety and the P-H bond, which allows various structural modifications: (i) for 1a, by introduction of amino substituents, (ii) for 2a, by hydroxy- or aminoalkylation, by Michael addition or by P-arylation. These reactions present generally a good or even an excellent kinetic diastereoselectivity which can often be predicted by molecular models of the transition states.
New syntheses of 1-chloroalkylphosphinates
Morise, Xavier,Savignac, Philippe,Denis, Jean-Marc
, p. 2179 - 2185 (2007/10/03)
Different approaches to the synthesis of 1-chloroalkylphosphinates are described. Initially, we tried to extend a reaction described by Kabachnik for the preparation of chloromethylphosphinic acid chlorides [R1(Cl)P(O)CH2Cl] to C-substituted derivatives. We also considered the possibility of synthesizing the title compounds by routes already described for the formation of diethyl 1-chloroalkylphosphonates. Although these methods have allowed us to obtain several of the desired phosphinates, they suffer from limitations that restrict their synthetic applications. Finally, we have developed a more general approach that allows the formation of a wide range of phosphinates. It involves a selective P-C bond formation by reaction of MeMgCl and PhMgCl with phosphonochloridates, which are prepared by P-chlorination of 1-chloroalkylphosphonates.
