An unexpected product in attempted [4 + 2] cycloadditions of 
2,2-diethyl-4,5-dimethyl-2H-imidazole

Felderhoff, Michael; Sustmann, Reiner; Steller, Ingo; Boese, Roland

doi:10.1002/jlac.1995199509236

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An unexpected product in attempted [4 + 2] cycloadditions of 2,2-diethyl-4,5-dimethyl-2H-imidazole

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Felderhoff, Michael
Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Institut für Organische Chemie der Universität Essen, D-45117 Essen, Germany;

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Citation

Felderhoff, M., Sustmann, R., Steller, I., & Boese, R. (1995). An unexpected product in attempted [4 + 2] cycloadditions of 2,2-diethyl-4,5-dimethyl-2H-imidazole. Liebigs Annalen, 1995(9), 1697-1698. doi:10.1002/jlac.1995199509236.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-1DB5-0

Abstract

2,2-Diethyl-4,5-dimethyl-2H-imidazole 1, formally a 1,4-di-azadiene, does not produce [4 + 2] cycloadducts with various electronically-different dienophiles. In the presence of tri-fluoroacetic acid, it tautomerizes to 2,2-diethyl-4-methyl-5-methylene-3-imidazoline 2 and forms a dimer, the structure of which was determined by X-ray crystallography.