Formation of Carbonyl Compounds from Azines or Hydrazones with Active Manganese Dioxide
✍ Scribed by Priv.-Doz. Dr. G. Maier; cand. chem. U. Heep
- Publisher
- John Wiley and Sons
- Year
- 1965
- Tongue
- English
- Weight
- 226 KB
- Volume
- 4
- Category
- Article
- ISSN
- 0044-8249
No coin nor oath required. For personal study only.
✦ Synopsis
formamide complex [2], a mixture of 4-dimethylaminobenzaldehyde (2) and 4-dimethyIaminoisophthaldialdehyde
(3) is formed from which (3) may be isolated with 15-20 % yield. 3,5-Dimethyl-N,N-dimethylaniline (4) is even more easily diformylated. Under conditions which convert ( I ) exclusively to (2) [3] a mixture of about equal parts of unchanged (4), 4-dimethylamino-2,6-dimethylbenzaldehyde (S), and 4-dimethylamino-2,6-dimethylisophthaldialdehyde (6) is formed. The application of more than two moles of formylating agent results in the exclusive formation of the dialdehyde (6) in 60-80% yield. Monoformylation of (4) can only be achieved by adding one mole of the POC13-DMF complex at 5 "C very slowly to a large excess (5-10 moles) of the amine.