Synthesis of Phosphonic Acids Possessing Isoindolin-1-one Moiety: Unexpected Acid-Catalyzed C-P-Bond Cleavage

Abstract

Phosphonic acids bearing isoindolin-1-one moiety were synthesized by dehydrative aromatization of the corresponding epoxyisoindolyl phosphonates. A mechanism for the unexpected acid catalyzed dephosphorylation was proposed.

Keywords:

• Dehydrative aromatization
• dephosphorylation of phosphonic acid
• epoxyisoindolyl phosphonates

Dedicated to Professor Marian Mikołajczyk, CBMiM PAN, in Łódź, Poland, on the occasion of his 70th birthday.

This work was supported by the STCU grant No. 3558. In addition, we thank Dr. I. I. Gerus, Dr. A. O. Gudima, and Dr. Yu. M. Pustovit for helpful discussions.

Notes

∗δ_P(major diastereomer)/δ_P(minor diastereomer).