Cycloaddition/Aromatization Sequence for the Synthesis of 2,3-Disubstituted Benzenephosphonates

Abstract

The [4+2] cycloaddition of diethyl 1-phosphonobuta-1,3-diene with tetracyanoethylene, (E)-1,4-diphenylbut-2-ene-1,4-dione, N-phenylmaleimide, and dialkyl acetylenedicarboxylates is described. For the last two cases, treatment of the cycloadducts with nitrobenzene and a palladium catalyst allows the aromatization. Selective deprotections lead to phthalimide/phthalate derivatives with an ortho-phosphonic acid function.

Key words

cycloaddition - Diels–Alder reaction - phosphorus - bicyclic compounds - carboxylic acids - hydrolysis

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