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Unexpected Vinylcyclopropane Rearrangement: New Strategies toward Skipped Dienes Using Sulfonium Ylides : Unexpected Vinylcyclopropane Rearrangement: New Strategies toward Skipped Dienes Using Sulfonium Ylides

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Richald, Maximilien [UCL] Delbrassinne, Arnaud [UCL] Robiette, Raphaël [UCL]

Vinylcyclopropanes are key intermediates in organic chemistry which undergo several important rearrangements. Herein, we report on an unexpected rearrangement of vinylcyclopropane into skipped diene proceeding at room temperature and with high selectivity. Deuteration experiments indicate that the mechanism of this rearrangement involves regioselective ring‐opening of the cyclopropane ring followed by 1,2‐migration of an aryl group. Based on this transformation, two complementary strategies toward skipped dienes bearing an aryl group on the central center were developed using sulfonium ylides.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès libre
Publication date 2019
Language Anglais
Journal information "European Journal of Organic Chemistry" - Vol. 2019, no.23, p. 3779-3782 (2019)
Peer reviewed yes
Publisher Wiley
issn 1434-193X
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Keywords Physical and Theoretical Chemistry ; Organic Chemistry
Links
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Bibliographic reference Richald, Maximilien ; Delbrassinne, Arnaud ; Robiette, Raphaël. Unexpected Vinylcyclopropane Rearrangement: New Strategies toward Skipped Dienes Using Sulfonium Ylides : Unexpected Vinylcyclopropane Rearrangement: New Strategies toward Skipped Dienes Using Sulfonium Ylides. In: European Journal of Organic Chemistry, Vol. 2019, no.23, p. 3779-3782 (2019)
Permanent URL http://hdl.handle.net/2078.1/216713