Ene Reactions and [2+2]Cycloadditions of Nitrilium Salts with Alkenes

Autor:	W. Wirschun, Johannes C. Jochims, Rajab Abu-El-Halawa, Ahmed H. Moustafa, Clemens C. Freyhardt
Rok vydání:	1997
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Alkene Salt (chemistry) Organic chemistry Nitrilium Medicinal chemistry Alkyl Cycloaddition Ene reaction
Zdroj:	Journal für Praktische Chemie/Chemiker-Zeitung. 339:615-622
ISSN:	1521-3897 0941-1216
DOI:	10.1002/prac.199733901110
Popis:	N-Alkylnitrilium salts (1) undergo ene reactions with electron-rich di- and higher substituted alkenes 2 to afford either 2-azoniaallene salts (3, 6, 9, 11) (the nitrilium salt reacting as ene and the alkene reacting as enophile) or 1-azonia-1,4-pentadiene salts (10, 12) (the alkene reacting as ene and the nitrilium salt reacting as enophile). Competing with ene reactions tri- and tetrasubstituted alkenes and N-alkylnitrilium salts undergo [2+2]cycloaddition to furnish azetinium salts (8, 13). In solution, alkyl substituted 2-azoniaallene salts tautomerize to 2-azonia-1,3-butadiene salts (4, 5, 7). The constitutions of the 2-azoniaallene salt 6c and the azetinium salt 8 were secured by X-ray crystallographic analyses.
Databáze:	OpenAIRE
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