The generation of carbonyl compounds from acetals and ketals by iodotrichlorosilane (ITCS)
β Scribed by Saad S. Elmorsy; M.V. Bhatt; Andrew Pelter
- Book ID
- 104224768
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- French
- Weight
- 200 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
Cheap and readily available iodotrichlorosilane (SiCl, I NaI) readily regenerates aldehydes and ketones from cyclic and acyclic acetals and ketals, in 20-60 min at ambient temperature.
The reaction is highly chemoselective as phenolic ethers and esters are not cleaved. The pathway for the process is unlike any previously proposed.
π SIMILAR VOLUMES
The use of acetals and ketals as direct precursors for organozinc carbenoid chemistry is illustrated by their direct conversion to alkenes in a one pot operation. Aryl acetals can also be used as precursors for the cyclopropanation ofcyclohexene.
## Abstract For Abstract see ChemInform Abstract in Full Text.
## The effectiveness of the [TiCp2(CF$O3)2] catalyst for the Sakurai reaction has been exploredfor a variety of allylic silanes reacting with orthoesters, ace&, ketals, aldehydes and ketones. The Sakurai reaction (eqs 1.2) is promoted by a variety of Lewis acid@ including TiQ, Alc13, BF3, MesSi R'
In the previous paper&, we described the formation of cinnamic acid derivatives from saturated aliphatic acids and aromatic compounds by palladium (II) salts. In the course of further investigation of these reactions, we found