2‐Aza‐1,3‐dienes. 2. Synthesis and Structure of a Stable Azomethine‐ylid.
Thermal treatment of 2‐(2′‐cyano‐2′‐methoxycarbonyl)methylide‐amino‐1‐morpholino‐cyclohexene results in the formation of a stable isomere. Its azomethine‐ylid structure is demonstrated from the spectroscopic data (UV., IR., 1H‐ and 13C‐NMR.). 1,3‐dipolar cycloaddition reactions of this ylid leads to spiropyrrolines.
The nucleophilic attack of hydroxylamine at the 5 position of 2‐aryl‐4‐trifluoroacetyl‐5‐amino‐oxazoles leads to a mixture of stereoisomeric isoxazolines. Dehydration of these isomeric isoxazolines in the presence of trifluoroacetic anhydride gives 3‐amino‐4‐acylamino‐5‐trifluoromethylisoxazoles. The structures and spectroscopic data of these compounds are discussed.
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