The effect of a-silyl substitution on the oxidation of alcohols by lead tetraacetate has been evaluated. Under typical conditions for converting alcohols to cyclic ethers, ct-hydroxysilanes are instead efficiently transformed into mixed acetyl-silyl acetals.
Lead tetraacetate oxidation of ketoximes and aldoximes
β Scribed by G. Just; K. Dahl
- Publisher
- Elsevier Science
- Year
- 1966
- Tongue
- French
- Weight
- 271 KB
- Volume
- 7
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Oxidation of aliphatic ketoximes (1) and aldoximes (2) by lead tetraacetate (Pb(OAcjq) has been reported to lead to unstable geminal nitrosoacetates and to dimeric nitrosoacetates, respectively, while a,S-unsaturated and arylaldoximes afforded oxime anhydride N-oxides and carbonyl compounds (3).
π SIMILAR VOLUMES
IN recent years, the oxidation of monohydric alcohols to tetrohydrofuran derivatives by lead tetraacetate has been studied extensively in steroids and used successfully to functionalize the "unactivated" Cl\* or Ctp angular methyl group (1,2). We have applied this type of reaction in the bridged rin
Attention has been focused on the oxidation of amines with metals in higher valencyl in order to obtain information on reactive species such as nitrenium ions, nitrogen radicals, and nitrenes.
## Lead tetmacetate oxidation of monohydric aIdloIs bearing a carbon-hydrogen bond in the 8 -position represents a valuable synthetic route to tetmhydrofurane derivatives l,2.