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Synthesis 1990; 1990(9): 763-767
DOI: 10.1055/s-1990-27008
DOI: 10.1055/s-1990-27008
paper
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Reactions of Nitrilium Salts with α,β-Unsaturated Carbonyl Compounds
Further Information
Publication History
Publication Date:
17 September 2002 (online)
Nitrilium salts 1 react with α,β-unsaturated ketones 7a and aldehydes 7f,h,j to furnish either 4H-1,3-oxazinium salts 5a-e or 6H-1,3-oxazinium salts 11f-i or N-acyl-1-azonia-1,3- butadiene salts 10j,k. The formation of these products is explained by a multistep reaction sequence starting with a [2+2] cycloaddition of the carbonyl double bond to the nitrilium triple bond. The constitution of 6H-1,3-oxazinium hexachloroantimonate 11i is confirmed by an X-ray structural analysis.