DOI

Diphenyl allenyl phosphonates are cyclized into 2,5-dihydro-1,2-oxaphosphol-2-ium ions in Brønsted acids (TfOH, H2SO4, FSO3H). These species have been studied by means of 1H, 13C, 31P NMR. The cations react with various nucleophiles (H2O, MeOH, EtOH, Et2NH, PhH) on the phosphorus atom. The obtained products are very labile and undergo decomposition. Contrary to Brønsted acids, under the action of Lewis acids AlX3 (X=Cl, Br), these diphenyl allenyl phosphonates lead to another kind of heterocycles, 2,5-dihydrobenzo[f][1,2]oxaphosphepine-2-oxides.

Original languageEnglish
Pages (from-to)4505-4510
Number of pages6
JournalChemistrySelect
Volume2
Issue number16
DOIs
StatePublished - 31 May 2017

    Research areas

  • 1,2-oxaphosphol-2-ium ions, allenes, Brønsted and Lewis acids, phosphaheterocycles, phosphorus electrophiles

    Scopus subject areas

  • Chemistry(all)

ID: 97790199