95735-85-6Relevant 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.
Novel photoacid generators for photodirected oligonucleotide synthesis
Serafinowski, Pawel J.,Garland, Peter B.
, p. 962 - 965 (2007/10/03)
Photodirected oligonucleotide synthesis uses either direct or indirect light-dependent 5′-deprotection. Both have been reported to give lower stepwise synthetic yields than conventional methods. The deficiency appears to be due to incomplete deprotection at the oligonucleotide 5′-position and, additionally in the case where photodirection is indirect and uses photogenerated photoacid to effect 5′-detritylation, the depurinating effects of strong acid. We have developed novel photosensitive-2-nitrobenzyl esters that on irradiation with near UV light generate α-chloro-substituted acetic acids, such as trichloroacetic acid, which are widely and successfully used in conventional solid-phase oligonucleotide synthesis. α-Phenyl-4,5-dimethoxy-2-nitrobenzyltrichloroacetate and α-phenyl-4,5-dimethoxy-2,6-dinitrobenzyltrichloroacetate showed appropriate photochemical characteristics and were used for photodirected synthesis of a variety of oligonucleotides, including (T)5, TATAT, TGTGT, (T)10, (AT)5, (CT)5 (GT)5 and (TGCAT)2 on a modified Millipore Expedite DNA synthesizer. The outcomes were compared with those obtained by use of directly added trichloroacetic acid (conventional synthesis). The stepwise yields for the two methods were essentially identical.
