Ring-opening reactions of cyclopropanes. Part 8.1 Nitrosation of donor-acceptor cyclopropanes

F Cermola, L Di Gioia, ML Graziano…

Index: Cermola, Flavio; Di Gioia, Lucrezia; Graziano, Maria Liliana; Iesce, Maria Rosaria Journal of Chemical Research, 2005 , # 10 p. 677 - 681

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Citation Number: 6

Abstract

The reaction of 2, 2-dialkoxycyclopropane-1-carboxylates 1a-d and monoalkoxycyclopropane 1e with NOCl gives isoxazoline-and/or isoxazole-3-carboxylates by regioselective ring-opening at C1-C2 bond. A mechanistic interpretation suggests the intermediacy of well-stabilised dipolar species.