Reactions of 2-phenyl-4 H-1, 3, 2-benzodioxaborin, a stable ortho-quinone methide precursor

JD Chambers, J Crawford…

Index: Chambers, Jeffrey D.; Crawford, Jason; Williams, Haydn W. R.; Dufresne, Claude; Scheigetz, John; et al. Canadian Journal of Chemistry, 1992 , vol. 70, # 6 p. 1717 - 1732

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Citation Number: 47

Abstract

Thermolysis of 1-phenyl-4 H-1, 3, 2-benzodioxaborins generated the corresponding ortho- quinone methides, which were found to undergo intermolecular cycloaddition reactions with ethyl vinyl ether, dihydropyran, β-methylstyrene, cyclohexene, and 1-ethoxy-1-z- trimethylsiloxy-1-propenes to give various substituted chromans. Intramolecular trapping of the quinone methides with an olefin led to the syntheses of several analogs of ...