ArticleAngewandte Chemie (International ed. in English)2017
Synthesis and Utilization of Nitroalkyne Equivalents in Batch and Continuous Flow.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Electrophilic and Radical Ability of Organic Nitrating Reagents.The Journal of organic chemistry · 2026Article
- Continuous Flow Acylation of (Hetero)aryllithiums with Polyfunctional N,N-Dimethylamides and Tetramethylurea in Toluene.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Synthesis and Utilization of Nitroalkyne Equivalents in Batch and Continuous Flow.Angewandte Chemie (International ed. in English) · 2017Article
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2 authors.
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Abstract
We report a method for overcoming the low stability of nitroalkynes through the development of nitrated vinyl silyltriflate equivalents. Because of their instability, nitroalkynes have only rarely been utilized in synthesis. The reactivity of these silyltriflates, which are prepared in situ, is exemplified by dipolar cycloaddition reactions with nitrones to give highly substituted 4-nitro-4-isoxazolines in high yields. This approach has proven general for several different alkyl and aryl substituted alkynes. In order to minimize the accumulation of potentially hazardous reaction intermediates, we have also developed a continuous flow variant of this method that is capable of carrying out the entire reaction sequence in a good yield and a short residence time.
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