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Synlett 1992; 1992(7): 581-584
DOI: 10.1055/s-1992-21423
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Halosulphonylation of Unsaturated Boronic Esters: Access to New Electron-Deficient Alkenes and Dienes

Nathalie Guennouni* , Christine Rasset-Deloge, Bertrand Carboni, Michel Vaultier
  • *Groupe de Recherche de Physicochimie structurale, UA. CNRS. 704, Université de Rennes I, Avenue du Général Leclerc, F-35042 Rennes, France
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Publication Date:
08 March 2002 (online)

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Sulphonyl halides undergo free radical addition to vinyl- and 1,3-dienylboronic esters (2-vinyl-1,3,2-dioxaborolanes 1 and 2-(1,3-alkadienyl)-1,3,2-dioxaborolanes 5] giving adducts which, in appropriate cases, afford upon treatment with base new β-sulphonyl α,β-unsaturated boronic esters [2-(2-p-toluenesulphonylethenyl)-1,3,2-dioxaborolanes 3 and 2-(4-p-toluenesulphonyl-1,3-butadienyl)-1,3,2-dioxaborolanes 6, respectively]. By using bromomethanesulphonyl bromide, the parent 1,3-butadienyl-2-boronic ester 8 was synthesized via a vinylogous Ramberg-Bäcklund rearrangement of the corresponding β-bromosulphone 7.