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Paper | Special issue | Vol 40, No. 2, 1995, pp.777-786
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S67
Silver Carbonate Promoted Reaction of Hydrazonyl Chlorides with Allylic Alcohols

Luisa Garanti, Giorgio Molteni, and Gaetano Zecchi

*Dipartimento di Chimica Organicane Industriale, dell'Universitè, Via Golgi 19, I-20133 Milano, Italy


The title reaction affords two main kinds of products: (i) pyrazole derivatives due to cycloaddition of a nitrile imine intermediate to the ethylenic bond; (ii) open-chain carbonyl compounds due to the electrophilic attack of a nitrilium-like carbocation to the ethylenic bond. Mechanistic possibilities are discussed.