Caveat in alkylative fragmentation of aldehyde tosylhydrazones of cyclic ethers
β Scribed by S. Chandrasekhar; M. Venkat Reddy; Mohamed Takhi
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 154 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
Tosylhydrazones of aldehydes at the a-position of cyclic ethers when exposed to carbon nucleophiles produce either ring opened alkylated olefinic alcohols and/or cyclic alkylated vinyl ethers, the ratio of which is dependent on nature of hydrazone and nucleophile used.
π SIMILAR VOLUMES
Tosylhydrazones of cyclic aminoaldehydes when exposed to aromatic and aliphatic Grignard reagents produce ring-opened acyclic unsaturated primary carbamates and carbamate alcohols in good yields.
## Abstract The unstrained 3βchloroalcohols **1a**, **2a** and **3a** do not undergo solvolytic fragmentation in neutral and weakly acidic 80% ethanol, only substitution and elimination products being formed by the limiting __S__~__N__~__1__β__E1__ mechanisms. This also applies to the corresponding