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Paper | Regular issue | Vol 71, No. 5, 2007, pp.1095-1105
Published online, 6th March, 2007
DOI: 10.3987/COM-07-11013
Reaction of Hydrazonoyl Chlorides to Trimethylsilyl Homoallyl Ethers

Paola Del Buttero, Giorgio Molteni,* Sara Mondini, and Alessandro Ponti

*Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy


Title reaction gave mainly 4,5-dihydropyrazole derivatives due to nitrilimine cycloaddition onto the ethylenic bond. Cycloaddition regioselectivity was good despite the electronic demands of the substituents placed to the ethylenic dipolarophile are quite similar. Metalated transition states have been proposed in order to account the observed regioselectivity. Highly substituted cyclopropanes were also formed due to the electrophilic attack of a nitrilium-like carbocation to the ethylenic bond.