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

✍ Scribed by Felderhoff, Michael ;Sustmann, Reiner ;Steller, Ingo ;Boese, Roland

Book ID
102368174
Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
221 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

2,2‐Diethyl‐4,5‐dimethyl‐2__H__‐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.

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