185751-27-3Relevant academic research and scientific papers
Sigmatropic Isomerizations in 2-Azaallyl Systems. XV. Peculiarties of N-Benzylarylcarboximidoyl Chloride Reaction with Ethyl Diphenylphosphinite
Onys'ko,Kim,Kiseleva,Sinitsa
, p. 1244 - 1247 (2007/10/03)
N-Benzyl derivatives of arylcarboximidoyl chloride react with ethyl diphenylphosphinite to form a mixture of the prototropic isomers Ph2P(O)C(C6H4X)=NCH2Ph and Ph2P(O)CH(C6H4X)N=CHPh (X = H, 3-F, 4-F). The irreversible Ph2P(O)C(C6H4X)=NCH2Ph → Ph2P(O)CH(C6H4X)N=CHPh prototropic isomerization takes place on heating. An alternative scheme of Ph2P(O)CH(C6H4X)N=CHPh formation includes 1,3-proton transfer in an intermediate quasiphosphonium imidoyl derivative and subsequent dealkylation. For Ph2P(O)CH(C6H4X)N=CHPh a thermolytic reversible transfer of the Ph2P(O) group in the C=N-C triad is found.
