Ipso nitration. XIX. Formation of cyclohexadiene adducts from nitration of 4-ethyltoluene and 1,4-diethylbenzene in nitric acid and acetic anhydride
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13
摘要:
Nitration of 4-ethyltoluenein acetic anhydride at -20° gives the diastereoisomers of 1-ethyl-4-methyl-4-nitrocyclohexa-2,5-dienylacetate and of 4-ethyl-1-methyl-4-nitrocyclohexa-2,5-dienyl acetate. Similarnitration of 1,4-diethylbenzene gives the diastereoisomers of1,4-diethyl-4-nitro-cyclohexa-2,5-dienyl acetate. Rearomatization of theadducts of p-ethyltoluene in trifluoroacetic acid-trifluoroacetic anhydridegives 4-ethyl-2-nitrotoluene from the 1-ethyl-4-methyl-4- nitro isomers and4-ethyl-3-nitrotoluene from the 4-ethyl-1-methyl-4-nitro isomers. In aqueousmethanol 2-ethyl- 5-methylphenyl acetate is obtained from the1-ethyl-4-methyl-4-nitro isomers and 5-ethyl-2- methyl-phenyl acetate from the4-ethyl-1-methyl-4-nitro isomers.
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DOI:
10.1071/CH9781241
被引量:
年份:
1978
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