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Unexpected [2 + 2] cycloaddition between the PO group of P-(2,4,6-triisopropylphenyl) P-heterocycles and dimethyl acetylenedicarboxylate

György Keglevich, Henrietta Forintos, Áron Szöllősy, Lásʐló Tőke

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Abstract

The reaction of 1-(2,4,6-triisopropylphenyl)-1,2-dihydrophosphinine 1-oxide 1d with dimethyl acetylenedicarboxylate (DMAD) affords, surprisingly, oxaphosphetene 3 instead of the expected Diels–Alder cycloadduct; the unusual reactivity of the trialkylphenylphosphine oxides towards DMAD seems to be of general value.

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What this paper is about

The reaction of 1-(2,4,6-triisopropylphenyl)-1,2-dihydrophosphinine 1-oxide 1d with dimethyl acetylenedicarboxylate (DMAD) affords, surprisingly, oxaphosphetene 3 instead of the expected Diels–Alder cycloadduct; the unusual reactivity of the trialkylphenylphosphine oxides towards DMAD seems to be of general value.

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Available abstract

The reaction of 1-(2,4,6-triisopropylphenyl)-1,2-dihydrophosphinine 1-oxide 1d with dimethyl acetylenedicarboxylate (DMAD) affords, surprisingly, oxaphosphetene 3 instead of the expected Diels–Alder cycloadduct; the unusual reactivity of the trialkylphenylphosphine oxides towards DMAD seems to be of general value.

Key concepts: Dimethyl acetylenedicarboxylate, Cycloaddition, Reactivity (psychology), Chemistry, Medicinal chemistry, Organic chemistry, Catalysis, Medicine

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Unexpected [2 + 2] cycloaddition between the PO group of P-(2,4,6-triisopropylphenyl) P-heterocycles and dimethyl acetylenedicarboxylate — Research Paper | ScholarLens