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Novel applications of N-sulfonyl-alkylamines in [2+4] cycloadditions by Ingo Tornus; Ernst Schaumann is a Chemistry article available to read on EtoBox.
What is Novel applications of N-sulfonyl-alkylamines in [2+4] cycloadditions about?
N-Sulfonylamine 2e was generated from the corresponding sulfamoyl chloride lc at -78 °C by triethylamine-inducod dehydrehalogenation or from the novel precursor 5 with a phthalimidyl leaving group at room temperature. Trapping of 2c from either source with 3-trimethylsiloxy-l,3butadiene (3) gave the expected [2+4] cycloadduct 4. However, the reaction of N-sulfonyl-alkylamines 2 with 2-aza-l,3-dienes 7 depended on the size of the alkyl group in 2 and on the reaction conditions. Thus, use of the heterocumulenes 2a,b (alkyl residue = Me, El) at -78 °C gave rise to the cycloadducts 8a,b regioselectively. In contrast, the reaction of 7 with 2c,d carrying a bulky isopropyl or tert.-butyl group provided the bissulfamoylated 2-aza-1,3-cliches 10a-e. On the other hand, starling from precursor 5 at room temperature also 2c reacted with the dienes 7 to forna the ring-closure products 8c,d.
Who reads Novel applications of N-sulfonyl-alkylamines in [2+4] cycloadditions?
It is typically read by researchers, students, and practitioners in Chemistry.
- Author
- Ingo Tornus; Ernst Schaumann
- Publisher
- Elsevier BV
- Published
- 1996
- Language
- EN
- Field
- Chemistry (Physical Sciences)