- Oxidation of benzylic alcohols and ethers to carbonyl derivatives by nitric acid in dichloromethane
-
Nitric acid in dichloromethane may be successfully employed for the oxidation of benzylic alcohols and ethers to the corresponding carbonyl compounds. The proposed method proved to be of general applicability, affording very good yields of aldehydes and ketones and showing interesting chemoselectivity in many instances, allowing competitive aromatic nitration to be avoided, as well as - in the case of aldehydes - any further oxidation to carboxylic acids. The reaction probably proceeds by a radical mechanism, the active species in the oxidation process being NO2. Competitive formation of nitro esters was observed in some cases, whereas poor results were obtained with allylic and non-benzylic substrates. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Strazzolini, Paolo,Runcio, Antonio
-
p. 526 - 536
(2007/10/03)
-
- Oxidative Cleavage of Ethers by Metallic Nitrates Supported on Silica Gel
-
Metallic nitrates supported on silica gel efficiently cleave and oxidize ethers to the corresponding aldehydes or ketones under mild conditions.Silica gel is essential for the efficient oxidation, and Cu(NO3)2 and Zn(NO3)2 are suitable for practical use.Overoxidation of the product aldehydes is not observed.In some cases alkyl nitrites are isolated in addition to the carbonyl compounds, and the decomposition of alkyl nitrites to the corresponding carbonyl compounds is promoted by the presence of metallic nitrates supported on silica gel.Mechanistic study suggests nitrogen dioxide is an active species.
- Nishiguchi, Takeshi,Bougauchi, Masahiro
-
p. 5606 - 5609
(2007/10/02)
-
- Tris(substituted amino) sulfonium salts
-
Trisaminosulfonium salts of the formula (R1 R2 N)(R3 R4 N)(R5 R6 N)S+ X- wherein the R groups are alkyl of 1-20 carbons and each alkyl has at least 2 alpha hydrogens and X is selected from the group (CH3)3 SiF2, Cl, Br, I, CN, NCO, NCS NO2 and N3, are soluble in organic liquids. They are useful as polymerization catalysts and as reagents to replace other atoms or groups in organic compounds with F, Cl, Br, I, CN, NCO, NCS, NO2 or N3.
- -
-
-
