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The correlation of some of the Friedel-Crafts' reaction

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McGechenJF_1930redux.pdf (11.78Mb)
Date
1930
Author
McGechen, John Finnie
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Abstract
 
 
1. The proportions of m- and p-tert.-butyl-toluenes produced in the reaction between tert.-butyl chloride and toluene with aluminium chloride as catalyst have been estimated.
 
2. The proportions of m- and p-tert.-butyltoluenes in the same reaction with ferric chloride as catalyst have been estimated.
 
3. The observation of Bialobrzewski was shown to be definitely wrong by proving that m-tert.-butyltoluene was a product of the reaction mentioned in (2), and that it was present to the extent of 65$ of the total monosubstituted derivatives.
 
4. The reaction between n-butyl chloride and toluene was carried out for the first time, and mand p-sec.-butyltoluenes shown to be products of the reaction.
 
5. The reactions between n-butyl chloride and both chloro- and bromobenzenes were carried out for the first time, and m- and p~derivatives of the halogeno-benzenes shown to be formed in both cases.
 
6. tert.Butyl chloride and bromobenzene, when allowed to react' in presence of aluminium chloride, were shown to produce m- and p-bromo-tert.-butylbenzenesin a proportion of 70% to 30% respectively, which disagrees with the result of Boedtker who reported that the p-derivative only was formed.
 
URI
http://hdl.handle.net/1842/35235
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