Formation of Adducts in the Nitration of p-Xylene. Exchange and Rearomatization Reactions of p-Xylene Adducts
1974 ◽
Vol 52
(23)
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pp. 3960-3970
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Keyword(s):
Nitration of p-xylene in acetic anhydride gives as the major product cis and trans isomers of the adduct 1,4-dimethyl-4-nitro-1,4-dihydrophenyl acetate (1) as well as 2-nitro-p-xylene. The acetoxynitro adducts 1a and 1b are stereospecifically cleaved to the hydroxynitro adducts 2a and 2b, respectively, by sodium methoxide. Acid-catalyzed exchange of OAc in 1 for OCH3, OCHO, OCH2C6H4CH3-p occurs and is nonstereospecific. Rearomatization of 1 gives 2-nitro-p-xylene, side-chain (benzylic) derivatives, and 2,5-xylyl acetate. The relevance of these reactions to side-chain substitution of arenes under electrophilic conditions is discussed.
1972 ◽
Vol 50
(24)
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pp. 3988-3992
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Keyword(s):
Keyword(s):
1967 ◽
Vol 45
(21)
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pp. 2547-2558
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Keyword(s):
1979 ◽
Vol 57
(14)
◽
pp. 1804-1813
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1984 ◽
Vol 62
(10)
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pp. 1945-1953
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Keyword(s):
Keyword(s):
Keyword(s):
1964 ◽
Vol 239
(8)
◽
pp. 2482-2488