Pummerer-like reaction of selenium(IV)-dichlorides. Synthesis of α-chloro-α-phenylselenenylketones and α,α-dichloro-α-phenylselenenylketones
✍ Scribed by Lars Engman; Joachim Persson; Ulf Tilstam
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 257 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Selenium(W)-dichlorides
1, readily available by treatment of methyl ketones with phenylselenium trichloride or selenium tetrachloride, were treated in methylene chloride with pyridine to give a-chloroselenides 2 in a Pummerer-like reaction. Sulfuryl chloride chlorination of these materials and repeated pyridine treatment similarly afforded a,a-dichloroselenides 4.
📜 SIMILAR VOLUMES
## Reaction of a,&unsaturated sulphoxides with trtfluoroacetic anhydri& gives a,j+bis(trifhwroacetoxy)thioethers in near-quantitative yields. Subsequent basic methanolysis gives monomeric and dimeric a-hydroxyaldehydes or ahydroxyketones, &pending on the nature of the 8-R group. The former undergo W
Sly1 enol ethers of ketones are alkylated with ethyl a-chloro-a-phenylseleno acetate la or with ethyl a-chloro-a-phenylseleno propionate lb, mediated by zinc bromide to give the corresponding a-phenylseleno-y-keto esters 3 in moderate to good yields.