Phosphonated bicycles bearing a N-N junction

Villemin, Elise;Herent, Marie-France;Marchand-Brynaert, Jacqueline
(2013) Heterocycles — Vol. 87, n° 3, p. 599-610 (2013)

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  • Villemin, EliseUCLouvain
    Author
  • Herent, Marie-FranceUCLouvain
    Author
  • Marchand-Brynaert, JacquelineUCLouvain
    Author
Abstract
The Diels-Alder reaction between diethyl 1-phosphono-1,3-butadiene and cyclic azo dienophiles, such as 4-phenyl- and 4-methyl-1,2,4-triazoline-3,5- diones and phthalazine-1,4-dione gave access to phosphonated bicyclic cycloadducts bearing a N-N junction. Various functionalizations (dihydroxylation, hydrogenation and phosphonic ester deprotection) have been performed with success. The selective N-N cleavage was not possible for the preparation of large heterocycles. The coordination properties of selected bicycles were tested by ESI-HRMS. © 2013 The Japan Institute of Heterocyclic Chemistry.
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Villemin, E., Herent, M.-F., & Marchand-Brynaert, J. (2013). Phosphonated bicycles bearing a N-N junction. Heterocycles, 87(3), 599-610. https://doi.org/10.3987/COM-12-12653 (Original work published 2013)