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

Elise Villemin; Jacqueline Marchand-Brynaert

doi:10.1055/s-0031-1289757

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(12): 1923-1927
DOI: 10.1055/s-0031-1289757

paper

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

Elise Villemin

Université catholique de Louvain, Institute of Condensed Matter and Nanosciences (ICMN), Molecules, Solids and Reactivity (MOST), Bâtiment Lavoisier, Place Louis Pasteur, L4.01.02, 1348 Louvain-la-Neuve, Belgium, Fax: +32(10)474168 eMail: Jacqueline.marchand@uclouvain.be

,

Jacqueline Marchand-Brynaert*

Université catholique de Louvain, Institute of Condensed Matter and Nanosciences (ICMN), Molecules, Solids and Reactivity (MOST), Bâtiment Lavoisier, Place Louis Pasteur, L4.01.02, 1348 Louvain-la-Neuve, Belgium, Fax: +32(10)474168 eMail: Jacqueline.marchand@uclouvain.be

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Abstract

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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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