Dihydronaphthalenes solvolysis

The specific acid-catalysed solvolysis of l-methoxy-l,4-dihydronaphthalene or 2-methoxy-l,2-dihydronaphthalene has been subjected to kinetic and product studies. The elimination product, naphthalene, predominates. 

Specific acid-catalysed solvolysis of l-methoxy-l,4-dihydronaphthalene or 2-methoxy-l,2-dihydronaphthalene in 25% acetonitrile in water has been found to yield mainly the elimination product, naphthalene, along with a small amount of 2-hydroxy-1,2-dihydronaphthalene, there being no trace of either the 1-hydroxy-1,4-dihydronaphthalene or the rearranged ether. The nucleophilic selectivity, ns/ hoh = 2.1 X 10", between added azide ion and solvent water has been estimated for the relatively stable = 1 x 10 s ) intermediate benzallylic carbocation for which the barrier to dehydronation is unusually low k = 1.6 x 10 ° s ), as evidenced by the large elimination-to-substitution ratio with solvent water as base/nucleophile. The kinetics of acid-catalysed solvolysis of 1-hydroxy-1,4-dihydronaphthalene and 2-hydroxy-1,2-dihydronaphthalene have also been studied. 

X 10", between added azide ion and solvent water has been estimated for the relatively stable = 1 x 10 s ) intermediate benzallylic carbocation for which the barrier to dehydronation is unusually low k = 1.6 x 10 ° s ), as evidenced by the large elimination-to-substitution ratio with solvent water as base/nucleophile. The kinetics of acid-catalysed solvolysis of 1-hydroxy-1,4-dihydronaphthalene and... 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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