Stereoselective azine formation in the decomposition of phenyldiazomethanes
β Scribed by Abelt, Christopher J.; Pleier, Jennifer M.
- Book ID
- 127021802
- Publisher
- American Chemical Society
- Year
- 1989
- Tongue
- English
- Weight
- 676 KB
- Volume
- 111
- Category
- Article
- ISSN
- 0002-7863
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π SIMILAR VOLUMES
Catalytic decomposition of phenyldiazomethane in S&ill's bases is found to proceed via formation of trans-1,3dipole (azomethine ylide) as an intermediate product. Depending on the size and quantity of the substituents, the ylide undergoes either cyclization in controtatory sense to cia-aziridine or
The reactions of several phenyldiazomethanes with chloranil gave stilbenes and Spiro-oxetanes at 20Β°C. Stilbenes were major products and the thermodynamically less stable cis-isomers prevailed about 2 to 3 times more than trans-ones depending on the solvents and the substituents of phenyldiazomethan
During the course of our investigations into the addition of alkali metals to carbon-nitrogen double bonds (1, 2, 3), we have examined the behaviour of benzophenone azine(