✦ LIBER ✦
Silicon-directed beckmann fragmentation. Catalytic cleavage of cyclic β-trimethylsilylketoxime acetates with trimethylsilyl trifluoromethanesulfonate
✍ Scribed by Hisao Nishiyama; Koji Sakuta; Noriyuki Osaka; Kenji Itoh
- Book ID
- 104221573
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- French
- Weight
- 204 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Cyclic (E)-B-trimethylsilylketoxime acetates were effectively cleaved by a catalytic action of trimethylsilyl trifluoromethanesulfonate to give the corresponding unsaturated nitriles. The fragmentation in the Beckmann rearrangement is completely controlled and directed by trimethylsilyl group to lead regio-and stereospecific formation of the double bond.
Under the same reaction condition, (Z)-isomers of the 8-IMS-oxime acetates were almost recovered (-90%).