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Beilstein J. Org. Chem. 2010, 6, 1035–1042, doi:10.3762/bjoc.6.118
Graphical Abstract
Scheme 1: Mechanism of dehydration of benzene-1,2-dihydrodiol.
Figure 1: Reactivity ratios for acid-catalyzed reaction of arene dihydrodiols.
Figure 2: Substrates for solvolysis measurements.
Scheme 2: Products of solvolysis and (ester) hydrolysis of trans-1-trichloroacetoxy-2-methoxy-1,2-dihydronaph...
Scheme 3: Products of solvolysis of trans-1-chloro-2-hydroxy-1,2,3,4-tetrahydronaphthalene.
Figure 3: Rate constants for aqueous solvolyses.
Figure 4: Cis/trans reactivity ratios for β-hydroxycarbocation forming reactions.
Figure 5: Comparison of the effect of a β-hydroxy group on the reactivity of cis and trans di- and tetrahdron...
Scheme 4: ‘Aromatic’ hyperconjugation for the benzenium ion.
Scheme 5: Stereochemistry of carbocation formation from solvolysis of cis-1-trichloroacetoxy-2-hydroxy-1,2-di...