Synthesis of cyclic ethers by rhodium carbenoid cyclisation
β Scribed by Julie C Heslin; Christopher J Moody; Alexandra M.Z. Slawin; David J Williams
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 208 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
## Sumnary: Treatment of the diazo-compounds (31, obtained in two steps from readily available hydrazine derivatives (11, with a catalytic amount of rhodium (II) acetate
Rhodium (II) acetate catalysed decomposition of the diazo sulphoxides (1) and ( 3) gives the cyclic sulphoxonium ylides ( 2) and ( 4); the structures of ( 2~) and (4a) were confirmed by X-ray crystallography.
Key Words\_dulltan aceme. ftran syntbsi.s, diazaxwpound. Abrtrrtr Diawcydohamwddus undergo dipohr cyclwdditioru with subsMufedacttylenes w provide 2-\* mhdbtai ietmhpirohw~4-oncs and with allencs to provide 2(H)\_3-me~hykned&d+mnmes.
Copper carbenoids undergo efficient intramolecular insertion into ally1 ethers, and 'the resulting ylide-type species rearrange to furnish cyclic ethers (ring sizes 6-8) in high yield. Copper(E) hexafluoroacetylacetonate is an extremely efficient catalyst for this reaction, and use of this complex