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Paper | Regular issue | Vol 87, No. 3, 2013, pp.599-610
Published online, 15th January, 2013
DOI: 10.3987/COM-12-12653
Phosphonated Bicycles Bearing a N-N Junction

Elise Villemin, Marie-France Herent, and Jacqueline Marchand-Brynaert*

*Institute of Condensed Matter and Nanosciences (IMCN), Université Catholique de Louvain, Bâtiment Lavoisier, place Louis Pasteur 1, B-1348 Louvain-la-Neuve , Belgium

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 with a nitrogen-nitrogen junction. Various fonctionalizations (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.