Abstract
3-Chloro-3-(dimethylphosphono)isobenzofuranone (I), obtained by the reaction of phthaloyl dichloride with (MeO)3P can be monodemethylated to sodium 3-chloro-3-(methylphosphono)isobenzofuranone (2) by Nal, or hydrolyzed to 3-hydroxy-3-(methyl)phosphonoiso- benzofuranone (3 and 4), depending on the reaction conditions. The 31P nmr spectra of hydroxyphosphonoisobenzofuanones 3 and 4 were found to be pH dependent. Raising the pH of the solutions to 10 caused reversible changes in the spectra of 3 (31P δ = 10.2 ppm) and 4 (31P δ = 8.96 ppm) consistent with opening of the isobenzohranone ring and the formation of orrho-(phosphonoformyl)benzoate anions 5 (31P δ = 0.89 ppm) and 6 (31P δ = 0.19 ppm). Analogous changes were also observed in the 31C nmr spectra of the compounds. 3-Chloro-3 (dimethy1phosphono)-isobenzohra-none (1) reacts rapidly with aliphatic mines and with amino acids at room temperature to give phthalimides in high yields thus providing a new convenient sythetic method to such compounds. Ackowledgment J. K. thanks the Rabin Foundation in Denmark for a generous grant.
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