| Autor: |
Merey, Gokce, Kubilay, H Nur, Anac, Olcay |
| Zdroj: |
Chemistry Letters; April 2021, Vol. 50 Issue: 4 p668-671, 4p |
| Abstrakt: |
Diazocarbonyl compounds are versatile precursors of carbenes leading to various structures by using several metal catalysts, especially copper and rhodium salts. In this study, eight different diazocarbonyls having N-O moiety were used. The N-O tethered structures were preferred because they may allow some useful transformations of the final products into valuable compounds via N-O cleavage. In the presence of a double bond on the –OR function of the starting diazo compound, CuCl/AgSbF6catalyst yielded only cyclopropyl fused oxazinane/oxazepane derivatives over cyclopropanation while Rh2(OAc)4catalyst was giving mainly isooxazolidinones via C-H insertion.A comparative reactivity study of CuCl/AgSbF6and Rh2(OAc)4catalysts was conducted. A clear catalyst preference was observed towards isoxazolidinone and cyclopropyl fused oxazinane/oxazepane derivativatives. In the presence of double bond, Rh2(OAc)4gave predominantly insertion reaction while CuCl/AgSbF6mixture solely yielded cyclopropanation. Moreover, N-O moieties on the structures allow easy conversion to useful intermediates via mild N-O bond cleavage. |
| Databáze: |
Supplemental Index |
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