183230-90-2Relevant academic research and scientific papers
Sigmatropic isomerizations in 2-azaallyl systems. XIV. Prototropic and phosphorotropic rearrangements in the phosphorylation of N-benzylthen- and N-benzylfurimidoyl chlorides
Onys'ko,Kim,Kiseleva,Sinitsa
, p. 911 - 916 (2007/10/03)
Reaction of N-benzylthen- and N-benzylfurimidoylchlorides with alkoxy derivatives of univalent phosphorus is accompanied by an irreversible 1,3-prototropic rearrangement to form (phosphorylated benzalimines. The latter undergo a reversible phosphorotropic rearrangement in the azaallyl triad under thermolysis or with catalysis with boron trifluoride etherate. 2-Furyl derivatives prefer the phos phorotropic form with the heteryl and phosphorus-containing substituents attached to the same carbon atom of the C=N-C triad, while in 2-thienyl derivatives the tautomer with the heteryl and the phosphorus-containing substituents at different carbon atoms of the triad dominates.
