[}3+2]-CYCLOADDITIONS OF 1-AZA-2-AZONIAALLENE CATIONS TO MULTIPLE BONDS

Faculty Science Year: 1993
Type of Publication: Article Pages: 9973-9986
Authors:
WANG, QR, AMER, A, JOCHIMS, JC, MOHR, S, ERTEL, E
DOI: 10.1016/S0040-4020(01)80194-0
Journal: TETRAHEDRON PERGAMON-ELSEVIER SCIENCE LTD Volume: 49
Research Area: Chemistry ISSN ISI:A1993ME21200005
Keywords : [}3+2]-CYCLOADDITIONS , 1-AZA-2-AZONIAALLENE CATIONS , MULTIPLE BONDS    
Abstract:
Hydrazones of ketones, 1, are transformed into 1-chloroalkylazo compounds, 2, which react with Lewis acids to give transient 1-aza-2-azoniaallene salts, 3. The cations 3 react with with acetylenes, olefins, isocyanates, carbodiimides, and nitriles under {[}3+2]-cycloadditions. The cycloadducts undergo consecutive reactions, e.g. {[}1,2]-shifts of alkyl groups.
    
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