Abstract
Diazoamides 1a and 1b were prepared from 2-(O-allyl)- and 2-(S-allyl) anilines 2 respectively. Copper(II) catalysed decomposition of 1 resulted in formation of benzofused heterocycles 7 by [2,3]-rearrangement of the intermediate ylide. Rhodium(II) perfluorbutyramide catalysed reaction, however, gave mainly the indoles 8, 9 whereas rhodium(II) acetate catalysed reaction resulted in a mixture of products, with p-lactams formed by intramolecular C-H insertion predominating. Catalysed decomposition of N-pyridyl diazoamide 13 gave the stable pyridinium ylide 14, (C) 1998 Elsevier Science Ltd. All rights reserved.
| Original language | English |
|---|---|
| Pages (from-to) | 9689-9700 |
| Number of pages | 12 |
| Journal | Tetrahedron |
| Volume | 54 |
| Issue number | 33 |
| Publication status | Published - 13 Aug 1998 |
Keywords
- carbenes and carbenoids
- ylides
- catalysis
- C-H INSERTION
- CARBON-HYDROGEN INSERTION
- ALPHA-DIAZOCARBONYL COMPOUNDS
- RHODIUM(II) CARBOXYLATE
- ORGANIC-SYNTHESIS
- CYCLOPENTANE CONSTRUCTION
- STEREOSELECTIVE SYNTHESIS
- CYCLOADDITION REACTIONS
- CARBENOID REACTIONS
- DIAZO-COMPOUNDS
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