Thermodynamically unstable enols. 2-Methyl-2-penten-3-ols from 4-isopropylidene-5,5-dimethyl-2-dimethylamino-1,3-dioxolane
✍ Scribed by Schmidt, Erich Alfred; Hoffmann, H. M. R.
- Book ID
- 126842265
- Publisher
- American Chemical Society
- Year
- 1972
- Tongue
- English
- Weight
- 709 KB
- Volume
- 94
- Category
- Article
- ISSN
- 0002-7863
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📜 SIMILAR VOLUMES
In the chiral title compound, C 33 H 42 N 4 O 2 S 2 , the dihedral angle between the imidazole ring planes is 79.47 (17) . The packing is consolidated by van der Waals forces and weak C-HÁ Á ÁS interactions.
## Abstract The racemic sesquiterpenoid alcohol **7** was synthesized in four steps (27% overall yield) from the cyclohexadienone **1**. The key steps are the regioselective addition of the pentadienyllithium **2** to **1** and the __Lewis__‐acid induced aromatization **4** → **6**.
**Structure of the adduct from 3‐dimethylamino‐2,2‐dimethyl‐2__H__‐azirine and 3‐methyl‐2,4‐diphenyl‐1,3‐oxazolium‐5‐olate** 3‐Dimethylamino‐2,2‐dimethyl‐2__H__‐azirine (**1**) reacts with 3‐methyl‐2,4‐diphenyl‐1,3‐oxazolium‐5‐olate (**5a**) to give a 1:1 adduct (**7**) in a 88% yield. Its crystal