92074-50-5Relevant academic research and scientific papers
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.
Organophosphorus Compounds. XX. Approaches to the Synthesis of 2,3-Dihydro-1H-1.2-benzazaphospholes Involving C-C and C-P Ring Closure
Collins, David J.,Drygala, Peter F.,Swan, John M.
, p. 1009 - 1021 (2007/10/02)
Reaction of chloromethylphosphonic dichloride (9) with N-methylaniline gave N,N'-dimethyl-N,N'-diphenylchloromethylphosphonodiamide (10) which upon treatment with aluminium chloride underwent intramolecular Friedel-Crafts alkylation to afford 1-methyl-2-(N'-methyl-N'-phenylamino)-2,3-dihydro-1H-1,2-benzazaphosphole 2-oxide (13a).Similarly, N-methyl-N-phenyl(chloromethyl)phenylphosphinamide (15) was cyclized to give 1-methyl-2-phenyl-2,3-dihydro-1H-1,2-benzazaphosphole 2-oxide (13b). Some unsuccessful approaches to this heterocyclic ring system are also reported.
