15539-79-4Relevant academic research and scientific papers
Oxidation of benzylic alcohols and ethers to carbonyl derivatives by nitric acid in dichloromethane
Strazzolini, Paolo,Runcio, Antonio
, p. 526 - 536 (2007/10/03)
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.
Ozone-mediated Nitration of Alkylbenzenes and Related Compounds with Nitrogen Dioxide
Suzuki, Hitomi,Murashima, Takashi,Kozai, Iku,Mori, Tadashi
, p. 1591 - 1598 (2007/10/02)
In the presence of ozone, nitrogen dioxide exhibits a strong nitrating ability for alkylbenzenes at low temperatures, converting them into the corresponding nitro derivatives in high yield.The addition of a protonic acid as catalyst enhances considerably the ability of this nitrating system and leads to a good yield of polynitro compounds.The reaction is clean and proceeds rapidly without any accompanying side-chain substitution or aryl-aryl coupling.It shows no kinetic dependence on the concentration of substrates and, as far as can be judged from relative reactivities and isomer distributions of products, it gives the appearance of being an electrophilic aromatic process.A possible role for nitrogen trioxide has been suggested as the initial electrophilic agent for the nitration of alkylbenzenes.
