The ene reaction of 5-allyl-2ϵ-hydroxy-5α-cholestan-3-one: An unusually facile ene reaction
✍ Scribed by Brian A. Marples; Christopher D. Spilling
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 219 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
The ene reaction of the unsaturated acyloins ( 8) occurs smoothly at llO°C demonstrating the greater reactivity of the acyloin versus the analogous ketone (4).
📜 SIMILAR VOLUMES
Sa-cholestane-5,6B\_dlol with B&K/B&H, \* This doublet is clearly resolved in the 3COMHz spectrum but only the up-field branch is resolved in the 9OMHs spectrum.
## Abstract Dehydrochlorination of chlorinated 5‐hydroxy‐2‐oxabicyclo[3.2.0]heptan‐4‐ones, 3a‐c, which were obtained from the photo[2+2]cycloadditions between 4‐hydroxy‐3(2__H__)‐furanone 1 and chloroethylenes, with triethylamine gave 2‐ethenyl‐3(2__H__)‐furanones 4a,b or 2‐(2‐cyanoethyl)‐3(2__H__)
During the attempted preparation of the p-toluenesulphonylhydrazone of enone 2 it has been established that a reductive side reaction occurs -probably brought about by di-imide, arising from the thermal decomposition of p-toluenesulphonylhydrazine. In connection with our studies 1 directed towards t