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By Satoshi Inagaki (auth.), Satoshi Inagaki (eds.)

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The hexatriene is polarized by unsymmetrical substitution with the C=O group, and further activated by coordination with Lewis acid. The catalyzed reaction is polar. The similarity between the catalyzed and the photochemical reactions can be understood if polar reactions belong to the pseudoexcitation band as has been proposed in Sect 1. , electrophilic aromatic substitution (Scheme 9). 1 S. Inagaki Delocalization Band No electrophilic aromatic substitution reactions of toluene, ethylbenzene, and cumene occur with BBr3 in the dark: the electrophile is too weak for these reactions.

This is a polar reaction in the pseudoexcitation band. According to the calculations at high levels of theory, the [4+2] cycloaddition reactions of dienes with the singlet (1Dg) oxygen follow stepwise pathways [37, 38]. These results, which were unexpected from the Woodward–Hoffmann rule and the frontier orbital theory, suggest that the [4+2] cycloadditions of the singlet (1Dg) oxygen could be the reactions in the pseudoexcitation band. 4 Cycloisomerization of Conjugate Polyenes According to the Woodward–Hoffmann rule [6, 7], conjugate polyenes with 4n and 4n+2 π electrons undergo cyclizations in conrotatory and disrotatory fashions under the thermal conditions, respectively.

A strong acceptor TCNE undergoes [2+2] rather than [4+2] cycloaddition reactions even with dienes. 1,1-Diphenylbutadiene [20] and 2,5-dimethyl-2,4-hexadiene (Scheme 5) [21] afford mainly and exclusively vinyl cyclobutane derivatives, respectively. In the reactions of 2,5-dimethyl-2,4-hexadiene: (1) the observed rate constant, kobs, is greater for chloroform solvent than for a more polar solvent, acetonitrile; (2) the trapping of a zwitterion intermediate by either methanol or p-toluenethiol was unsuccessful; (3) radical initiators such as benzyl peroxide, or radical inhibitors like hydroquinone, have no effect on the rate; (4) the entropies of activation are of A Mechanistic Spectrum of Chemical Reactions NC 7 CN CN CN + CN NC CN CN Scheme 5 Preference of [2+2] over [4+2] cycloaddition reactions in the pseudoexcitation band large negative value.

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