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Theoretical Studies on the Acid-catalysed Aromatization of Benzene-cis-1,2-dihydrodiols by Chang Kon Kim; Dong Soo Chung; Kyoo Hyun Chung; Bon-Su Lee; Ikchoon Lee is a Chemistry article available to read on EtoBox.

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## Abstract Theoretical studies on the acid‐catalysed dehydration of 15‐substituted dihydrodiols were carried out using the AM1 method. In agreement with the experimental results, the rate‐limiting step is dehydration of the protonated diols, R^+^, and the __o__‐phenol‐forming pathway (path 1) is favoured both kinetically and thermodynamically over __m__‐phenol product formation. The transition state for path 1 (TS 1) is found to be at an early position (__ca__ 23% progress) along the reaction coordinate and a better correlation of the rate constant is obtained with σ^+^. Three resonance forms can exist for the benzenonium intermediate but the contribution of one form is dominant in the later TS, which resembles the cationic intermediate. The contribution of the other two, however, weakens the σ^+^ effect of +M subsituents. The σ~P~ correlation of the rate constant in acid solution is therefore suggestive of a later TS resembling the cationic intermediate which is stabilized by solution.

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Author

Chang Kon Kim; Dong Soo Chung; Kyoo Hyun Chung; Bon-Su Lee; Ikchoon Lee

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0894-3230)

Published

1995

Language

EN

Field

Chemistry (Physical Sciences)