Cycloaddition/aromatization sequence for the synthesis of 2,3-disubstituted benzenephosphonates

Villemin, Elise;Marchand-Brynaert, Jacqueline
(2012) Synthesis : journal of synthetic organic chemistry — Vol. 44, n° 12, p. 1923-1927 (2012)

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  • Villemin, EliseUCLouvain
    Author
  • Marchand-Brynaert, JacquelineUCLouvain
    Author
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. © Georg Thieme Verlag Stuttgart · New York.
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Villemin, E., & Marchand-Brynaert, J. (2012). Cycloaddition/aromatization sequence for the synthesis of 2,3-disubstituted benzenephosphonates. Synthesis : journal of synthetic organic chemistry, 44(12), 1923-1927. https://doi.org/10.1055/s-0031-1289757 (Original work published 2012)