Tetrahedron

Reactivity of 3, 6-dimethoxy-3, 6-dimethylcyclohexa-1, 4-diene: nuclear versus benzylic nucleophilic substitution

F Alonso, I Barba, M Yus

Index: Alonso, Francisco; Barba, Isidoro; Yus, Miguel Tetrahedron, 1990 , vol. 46, # 6 p. 2069 - 2080

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Citation Number: 16

Abstract

The treatment of cis/trans-3, 6-dimethoxy-3, 6-dimethylcyclo-hexa-1, 4-diene (ca. 1/1 mixture; easily prepared electrochemically in multigram scale from p-xylene) under acidic conditions (acetic, trifluoroacetic, sulfuric, or a Lewis acid) yields almost exclusively 2- methoxy-1, 4-dimethylbenzene 4, through a transposition reaction. The use of aqueous hydrochloric or hydrofluoric acid gives 2, 5-di-methylphenol 12, and with hydrogen ...