Napthalene electrophilic substitution

El and E2 mechanisms, 130 Electron-dot structures, 2 Electronegativity, 21 Electrophiles, 35, 44, 47 Electrophilic substitution of arenes, 205 in napthalene, 213 Elimination, 34 1,2-Elimination, 91 Enantiomers, 69 conditions for, 80 conformational, 80 Enamines, 315, 378 Enolsilanes, 396 Enthalpy, 36 diagrams, 40, 49 Entropy, 36... 

All these procedures in the benzenoid series are based on electrophilic substitution while with napthalene compounds nucleophilic substitution has been employed as seen in the following examples. 2-Naphthol in anhydrous tetrahydropyran was treated rapidly over 2 mins, with butyllithium (2 moles) in pentane at 20-25°C. The solution was stirred for 4 hours, cooled to 0 C and after the addition of dimethyidisulphide in tetrahydropyran, the mixture was stirred for 2.5 hours to complete reaction to afford, after acidic work-up, 2-hydroxy-3-(methylthio)naphthalene in 83% yield (ref. 119). 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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