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• W2038171661 abstract "N,N-Bis(trimethylsilyl)ynamines 1 react with dimethyl acetylenedicarboxylate (2) in a molar ratio of 1:2 to afford 3-cyclopropenylfurans 3. Configuration and conformation of 3a are confirmed by X-ray crystallography. Addition of a further mol of 1 furnishes the fumarates 4. With ketenes 5 (5c, d are prepared in situ) a competition between the formation of cyclic butenone derivatives 6 and allenic imidates 7 is observed, depending on the substitution pattern of 1. After hydrolytic workup, the corresponding amides 10 or the vinylogous amides 9 are obtained in good yield. These experiments indicate that the silylated ynamines 1 show a completely different, more selective reactivity towards dimethyl acetylenedicarboxylate compared to N,N-dialkyl-substituted ynamines, yielding furan derivatives instead of anilines. Towards ketenes, however, a similar cycloaddition reactivity as for N,N-dialkylynamines is observed." @default.
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• W2038171661 date "1994-07-01" @default.
• W2038171661 modified "2023-10-16" @default.
• W2038171661 title "<i>N,N</i> ‐Bis(trimethylsilyl)ynamines: Cycloaddition Reactions with Dimethyl Acetylenedicarboxylate and Ketenes" @default.
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• W2038171661 doi "https://doi.org/10.1002/cber.19941270718" @default.
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