Reaerangements in a series of polymethylbenzenonium ions

Shubin, V. G.; Chzhu, V. P.; Rezvukhin, A. I.; Koptyug, V. A.

doi:10.1007/bf01179730

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Protonation Of Phenols Lacking a Para Substituent1

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1974

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“…This is in accord with the known equilibrium position between 31 and 16 which lies heavily in favor of 16 (29)(30)(31).…”

Section: Discussionsupporting

confidence: 76%

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Protonation of Methyl Substituted Phenols in Super Acids

Childs¹,

Parrington²

1974

Can. J. Chem.

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The protonation of a series of methyl substituted phenols and anisoles in FSO3H has been examined. When the para position of the phenol is unsubstituted, protonation was found to take place exclusively at this site. A methyl group on C-4 reduces the basicity of this carbon such that protonation on C-2, C-6 or oxygen can now compete with para protonation. Despite claims to the contrary, in FSO3H no significant amount of meta protonation was observed for any of the phenols. In FSO3H–SbF5, 2,4,6-trimethylphenol is protonated on C-3 or C-5; however, it would appear that this meta protonation is accompanied by a modification of the hydroxy group by either further protonation or reaction with the Lewis acid SbF5.

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“…This is in accord with the known equilibrium position between 31 and 16 which lies heavily in favor of 16 (29)(30)(31).…”

Section: Discussionsupporting

confidence: 76%

“…protonated phenols and those of the protonated cyclohexadienones 15 and 16 confirms their structural assignment (28)(29)(30)(31).…”

Section: Protonation Of Phenols Lacking a Para Substituentsupporting

confidence: 59%