ipso Nitration. XXVII. The crystal structure and stereochemistry of 3-bromo-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate, 5-bromo-2-methyl-6-nitrocyclohexa-2,4-dienyl acetate, and 3-bromo-6-methyl-6-nitrocyclohexa-2,4-dienyl chloride
Keyword(s):
The adduct obtained on nitration of 4-bromotoluene in acetic anhydride is (Z)-3-bromo-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate. Its stereoselective rearrangement product, obtained on thermolysis in the presence of p-cresol, is (Z)-5-bromo-2-methyl-6-nitrocyclohexa-2,4-dienyl acetate. Reaction with hydrogen chloride in ether is also stereospecific and gives (Z)-3-bromo-6-methyl-6-nitrocyclohexa-2,4-dienyl chloride. The crystal structures of these compounds are reported.
1993 ◽
Vol 48
(5)
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pp. 571-576
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2021 ◽
Vol 236
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pp. 11-21
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1975 ◽
Vol 31
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pp. 2508-2509
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1977 ◽
Vol 33
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pp. 2258-2263
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