74894-52-3Relevant academic research and scientific papers
π-Facial selectivity in nucleophilic additions to 4,4-disubstituted dienones: Experimental support for electrostatic control
Wipf, Peter,Kim, Yuntae
, p. 11678 - 11688 (2007/10/02)
The 4,4-disubstituted cyclohexadienones 5-10 and 32 were prepared by hypervalent iodine oxidation of the corresponding phenols. Our study of the facial selectivity in nucleophilic carbonyl additions provided experimental evidence for dominant dipolar cont
Reactions of the 1-hydroxy-1,4-dimethylcyclohexadienyl cation, an intermediate in the solvolysis of 1,4-dimethyl-4-nitrocyclohexa-2,5-dien-1-ol
Fischer, Alfred,Henderson, George N.,Smyth, Trevor A.
, p. 1093 - 1101 (2007/10/02)
Solvolysis of 1,4-dimethyl-4-nitrocyclohexa-2,5-dien-1-ol in mixed aqueous organic solvents gives the diastereomers of 1,4-dimethylcyclohexa-2,5-dien-1,4-diol, 1,4-dimethylcyclohexa-3,5-diene-1,2-diol, 2-nitro-p-xylene, 2,4-dimethylphenol (all derived from the title cation, itself formed by ionization of the nitro group as nitrite), and 2,5-dimethylphenol.In aqueous methanol the diastereomers of 4-methoxy-1,4-dimethylcyclohexa-2,5-dienol are also obtained.Significant yields of 2,5-dimethylphenol are only obtained on the acid-catalyzed further reaction of the dienediol (or the methoxydienol) and involve the intermediate formation of 1,4-dimethylcyclohexa-3,5-diene-1,2-diol.In the absence of added base the acid released in the solvolysis catalyses this reaction and leads to the aromatization of the dienes.
