A novel cyclization reaction catalyzed by the Grignard reagent. : The intramolecular linking of an aromatic ring to the α-position of ketoxime
✍ Scribed by T. Taguchi; K. Miyano; Y. Shimizu; Y. Kawazoe
- Publisher
- Elsevier Science
- Year
- 1968
- Tongue
- French
- Weight
- 190 KB
- Volume
- 9
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Received in Japan 30 May 1968; reoeived in BK for publication 25 dune 1968)
The Grignard reaction of ketoximes has been well-known as a pr .aration method of aziridines(3).
The present study demonstrates that the cyclization.of a certain kind of ketoximes involving an aryl group is catalyzed by arylmagnesium halide. ?-Cyclohexyliden yclohexanone(4) was reacted with phenylmagnesium bromide in the stream of nitrogen using purif 3d ether as a solvent to afford 2-(1-phenyl)cyclohexylcyclohexanone(I), m.p. 64-68'(methanol), yield 65-75% and 6-(1-phenyl)eyclohaxyl-6-oxo-n-hexanoic acid(II), m.p. 8l'(petroleum benzine), yield 5-7%. Structural proof for II was