Reactions of β-alkoxyvinyl trihalogenomethyl ketones with triethyl phosphite

The Perkow reaction of triethyl phosphite and β-alkoxyvinyl trihalogenomethyl ketones, which have common acyclic or cyclic structural fragment: –O–CC–C(O)CX2Cl, yielded dienyl phosphates: –O–CC–C[OP(O)(OEt)2]CX2 where X = F or Cl, whereas γ-bromo-β-methoxy-α,β-unsaturated trifluoromethyl ketone CF3C(O)CHC(OMe)CH2Br gave diene CF3C[OP(O)(OEt)2]CH–C(OMe)CH2.

Graphical abstractThe Perkow reaction of triethyl phosphite and β-alkoxyvinyl trihalogenomethyl ketones, which have common acyclic or cyclic structural fragment: –O–CC–C(O)CX2Cl, yielded dienyl phosphates: –O–CC–C[OP(O)(OEt)2]CX2 where X = F or Cl.Figure optionsDownload full-size imageDownload as PowerPoint slide