Intramolecular “Hydroiminiumation and-amidiniumation” of alkenes: A convenient, flexible, and scalable route to cyclic iminium and imidazolinium salts

…, RD Dewhurst, B Donnadieu, G Bertrand

Index: Jazzar, Rodolphe; Bourg, Jean-Baptiste; Dewhurst, Rian D.; Donnadieu, Bruno; Bertrand, Guy Journal of Organic Chemistry, 2007 , vol. 72, # 9 p. 3492 - 3499

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Citation Number: 90

Abstract

Addition of a stoichiometric amount of HCl to alkenylaldimines,-formamidines, and-amidines results in the protonation of the sp2-nitrogen atom. The resulting alkenylaldiminium,- formamidinium, and-amidinium salts can be isolated and fully characterized, including single-crystal X-ray diffraction studies. Heating solutions of these salts induces ring closure cleanly and regioselectively via formal “exo” addition of the nitrogen-hydrogen bond to the ...