The interaction of 2-(5-methyl-2-phenyl-2h-1,2,3-diazaphosphol-4-yl)-4h-benzo[e]-1,3,2-dioxaphosphinin-4-one with activated carbonyl compounds. Synthesis of bis-heterocyclic systems containing di- and tetracoordinated phosphorus

GRAPHICAL ABSTRACT

ABSTRACT

The interaction of 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphinin-4-one with mesoxalic and trifluoropyruvic acids ethyl and diethyl esters, hexafluoroacetone and chloral proceeds with an exclusive participation of P(III) atom and allows to obtain 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-derivatives of 1,4,2- and 1,3,2-dioxaphosphepines as well as dichlorovinylphosphonate, being the product of Perkow reaction in the case of chloral.

KEYWORDS:

• Diazaphosphole
• benzodioxaphosphinine
• benzodioxaphosphepine
• chloral
• hexafluoroacetone
• Perkow reaction

Funding

The work was supported by Russian Foundation for Basic Research (grant 16-03-00451) and funded also by the subsidy allocated to Kazan Federal University for the state assignment in the sphere of scientific activities (No. 4.5888.2017/8.9).

Supporting information

Hydrogen bonds in the molecules of compounds 1, 5, 7 and figures of NMR spectra of compounds 1--3, 5--7 are included in the Supplemental Materials (Figures S 1 - S 57).