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| - Divergent Pathways in the Reaction of Hexamethylbenzene withDimethyldioxirane1,2
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| - Hexamethylbenzene (1) reacts with dimethyldioxirane(2) via three separate reaction pathways.In the major pathway the reaction proceeds through an arene oxidewhich is rapidly transformedto the oxepin valence tautomer. In the first example of thereaction of an oxepin with 2 the oxepinis oxidized to first the cis-dioxide and then to thetrioxide with the third oxide trans to theothertwo oxide rings. In a second competing pathway a methyl groupmigrates in the first producedarene oxide to give a hexamethyl-cyclohexadienone. This materialthen reacts rapidly with 2 togive a trans-diepoxide. The third reaction pathwayinvolves the C−H insertion reaction of 2.Thisprocess gives first the derived benzyl alcohol and then thecorresponding benzoic acid. Two otherminor products are also formed, one is rationalized as arising fromreaction of the arene oxidewith water. The other is a tricyclic compound of unknownorigin.
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