- Catalytic halodefluorination of aliphatic carbon-fluorine bonds
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A variety of halosilanes, in conjunction with aluminum catalysts, convert fluorocarbons into higher halocarbons. Bromination and iodination of fluorocarbons are more effective than chlorination in terms of yield and activity. The mechanism for the reaction is investigated utilizing experimental and computational evidence and preliminary results suggest an alternate mechanism to that reported for the related hydrodefluorination reaction.
- Goh, Kelvin K.K.,Sinha, Arup,Fraser, Craig,Young, Rowan D.
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p. 42708 - 42712
(2016/05/19)
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- Tele nucleophilic aromatic substitutions in 1-nitro-3- and 1,3-dinitro- 5-trichloromethylbenzene, and 3-trichloromethylbenzonitrile. A new synthesis of the 1,4-benzothiazine-3(4H)-one ring system from 3 nitrobenzoic acid
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3-Trichloromethylnitrobenzene 2, 1,3-dinitro-5-trichloromethylbenzene 13 and 3-trichloromethylbenzonitrile 18 react with sodium methoxide to give 4- methoxy-3-nitrobenzaldehyde 6, 4-methoxy-3,5-dinitrobenzaldehyde 15 and 5- dimethoxymethyl-2-methoxybenzonitrile 19, respectively. Compounds 2 and 13 react with methyl thioglycolate to afford dichloromethylacetates 7 and 16, respectively. These products are the result of tele nucleophilic aromatic substitution. Compound 18 reacted with methyl thioglycolate to give acetate 20 resulting from nucleophilic displacement of cyanide. Reductive cyclisation of 7 afforded benzothiazine 11. (C) 2000 Elsevier Science Ltd.
- Giannopoulos, Thomas,Ferguson, John R.,Wakefield, Basil J.,Varvounis, George
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p. 447 - 453
(2007/10/03)
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