77815-15-7Relevant academic research and scientific papers
15N Nuclear Polarisation in Nitration and Related Reactions. Part 8. The Mechanisms of Rearrangement of 2-Methyl-2-nitrocyclohexa-3,5-dienones
Ridd, John H.,Trevellic, Susan,Sandall, John P. B.
, p. 1073 - 1079 (2007/10/02)
A kinetic study has been carried out on the regiospecific rearrangement of 2-methyl-2-nitrocyclohexa-3,5-dienone to 2-methyl-6-nitrophenol in acetic anhydride containing 0.2percent sulfuric acid at -27.8 to -6.5 deg C.Related studies have been carried out
Preparation of and addition of carbanions to 6-methyl-6-nitrocyclohexa-2,4-dienones
Fischer, Alfred,Henderson, George N.,Sankararaman, S.
, p. 1244 - 1246 (2007/10/02)
Nitration of 2-methylphenols with nitric acid and trifluoroacetic anhydride in ether at -78 deg C gives 6-methyl-6-nitrocyclohexa-2,4-dienones that can be isolated.Carbanions add to 5,6-dimethyl-6-nitrocyclohexa-2,4-dienone to give the 5-substituted 2,3-dimethyl-2-nitrocyclohex-3-enone anion, which, with additional carbanion, gives the 5-substituted 2,3-dimethylphenoxide anion by elimination of nitrous acid.Key words: nitration, dienone, addition, carbanion, nucleophilic.
FORMATION OF DIENONES ON THE REACTION OF CRESOLS, XYLENOLS, AND 2-NAPHTHOL WITH NITROGEN DIOXIDE: OBSERVATION OF KETO TAUTOMERS OF NITROPHENOLS
Fischer, Alfred,Mathivanan, N.
, p. 1869 - 1872 (2007/10/02)
Reaction of o- and p-cresol, the xylenols, and 2-naphthol with nitrogen dioxide gives nitrocyclohexadienones and nitrophenols.Secondary nitrodienones, the keto tautomers of the nitrophenols, have been observed in several cases and are intermediates in the formation of the nitrophenols.
ipso Nitration. XXIV. Nitration of 2-methylphenols. Formation and rearrangement of 6-methyl-6-nitrocyclohexa-2,4-dienones
Cross, Gordon G.,Fischer, Alfred,Henderson, George N.,Smyth, Trevor A.
, p. 1446 - 1451 (2007/10/02)
Nitration of o-cresol and some mono-, di-, and trimethyl derivatives in acetic anhydride at -60 deg C gives 6-methyl-6-nitrocyclohexa-2,4-dienones.The dienones are more labile than the isomeric 4-methyl-4-nitrocyclohexa-2,5-dienones and, if the 2-position of the dienone is not blocked, undergo regiospecific rearrangement to 6-nitro-o-cresols. 2,3,6-Trimethyl- and 2,3,5,6-tetramethylphenol also give a 2,5-dienone with nitro attached to a secondary carbon.
IPSO NITRATION: NITRATION OF 2-ALKYLPHENOLS IN ACETIC ANHYDRIDE. FORMATION OF 6-ALKYL-6-NITROCYCLOHEXA-2,4-DIENONES
Fischer, Alfred,Henderson, George N.
, p. 4661 - 4662 (2007/10/02)
Low temperature nitration of 2-alkylphenols in acetic anhydride gives 6-alkyl-6-nitrocyclohexa-2,4-dienones.The dienones undergo a regiospecific rearrangement to give o-nitrophenols
