A novel fragmentation reaction of α,β-epoxyketones the synthesis of acetylenic ketones
✍ Scribed by Masato Tanabe; David F. Crowe; Robert L. Dehn
- Publisher
- Elsevier Science
- Year
- 1967
- Tongue
- French
- Weight
- 167 KB
- Volume
- 8
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
We wish to report that p-toluenesulfonylhydrazones of certain o,g%poxyketones undergo a novel fragmentation reaction to yield an acetylene and a ketone as shown in Scheme 1.
📜 SIMILAR VOLUMES
Allenoxyborinates, easily generated via the 1,4-addition of dicyclohexylborane to a,~acetylenic ketones, react in situ with excess starting ketone to afford stereodefined, functionalized trisubstituted olefins in high yields.
The Reaction of α,β-Acetylenic Ketones with Dicyclohexylborane: Stereoselective Synthesis of Functionalized Trisubstituted Olefins. -α,β-Acetylenic ketones (I) (6 compounds) undergo 1,4-addition of dicyclohexylborane to give allenoxyborinate intermediates which react with excess starting ketone to