Insertion reactions of alkenes with diterpenoid chromium aminocarbenes
| Autor: | Paul D. Woodgate, Hamish S. Sutherland |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
chemistry.chemical_classification
Steric effects Alkene Stereochemistry Organic Chemistry chemistry.chemical_element Ring (chemistry) Biochemistry Medicinal chemistry Terpenoid Enamine Inorganic Chemistry chemistry.chemical_compound Chromium Hydrolysis chemistry Materials Chemistry Physical and Theoretical Chemistry Carbene |
| Zdroj: | Journal of Organometallic Chemistry. 628:155-168 |
| ISSN: | 0022-328X |
| Popis: | Insertion reactions of electron-deficient alkenes with chromium aminocarbenes derived from podocarpic acid generally give aryl ketone products derived from ring opening of an aminocyclopropane and subsequent enamine hydrolysis, the exception being alkenyl sulphones which give products derived from insertion of the carbene into the β-CH bond of the alkene. Increasing steric hindrance due to the substituents on the aminocarbene nitrogen appears to result in higher yields of the insertion products. However, other factors such as stabilisation of the intermediate tetracarbonylaminocarbene may explain why morpholinocarbenes give superior yields of the insertion products. Propenoic acid, propenal or nitropropene give a 13-formyl-substituted diterpenoid. Electron-rich alkenes do not undergo insertion reactions with these aminocarbenes at 110°C. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect