Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Letter
CuCl/AgSbF6 and Rh2(OAc)4 Comparison for the Synthesis of N-O Tethered Three and Five Membered Rings via Diazo Chemistry
Gokce MereyH. Nur KubilayOlcay Anac
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Keywords: Carbenoid, Diazo, N-O moiety
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2021 Volume 50 Issue 4 Pages 668-671

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Abstract

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/AgSbF6 catalyst yielded only cyclopropyl fused oxazinane/oxazepane derivatives over cyclopropanation while Rh2(OAc)4 catalyst was giving mainly isooxazolidinones via C-H insertion.

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© 2021 The Chemical Society of Japan
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