Synthesis of a novel cage compound via oxidative rearrangement of a dihydronaphthofuran
β Scribed by Margaret A. Brimble; Richard J.R. Elliott; Peter Turner
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 305 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0040-4020
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β¦ Synopsis
Oxidative rearrangement of dihydronaphthofuran 5 with aqueous ceric ammonium nitrate afforded the cage compound 7 which decomposed to diol 8 upon standing at room temperature. An X-ray structure obtained for diol 8 confirmed the formation of this novel cage structure.
π SIMILAR VOLUMES
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We wish to report a facile thermal rearrangement of an N-aryl propynylamine oxide to an indole. The present study, to our knowledge, is the first report of such a rearrangement. Compound 1 (89.5%; m.p. 76-77)\* was prepared by the condensation of l-(4-chlorophenoxy)-4chloro-2-butyne3 with two moles
A SIZEABLE body of evidence has now accumulated suggesting that a number Of rearrangement reactions proceed via three-membered nitrogen-containing rings. For example, the Neber rearrangement of ketoxime tosylates, 1 the rearrangement of N,N-dichloro-set-alkylamines, 2-4 and the synthesis of a-amino