Synthesis of new α-hydroxyphosphonates and α-acetoxyphosphonates

ABSTRACT

A series of new α-hydroxyphosphonate (5–14) have been synthesized in high yields by reaction of β-chloro-α,β-unsaturated aldehydes (1–4) and trialkyl phosphite in the presence of chlorotrimethylsilane at room temperature under solvent-free conditions. In addition, compounds (5–14) were reacted with acetic anhydride in DBU to give the new α-acetoxyphosphonate derivatives (15–23). All these phosphonates (5–23) were obtained as mixtures of two (E and Z) isomers and fully characterized by multinuclear (¹H, ¹³C, and ³¹P) NMR, IR spectroscopy and HRMS.

GRAPHICAL ABSTRACT

KEYWORDS:

• α-Acetoxyphosphonate
• α-hydroxyphosphonates
• β-chlorovinyl aldehydes
• NMR
• TMSCl

Additional information

Funding

We are grateful to the Tunisian Ministry of High Education and Scientific Research for financial support (LR99ES14) of this research.