4.5 Article

2-[(Trimethylsilyl)methyl]benzyl Methanesulfonates: Useful Precursors for the Generation of o-Quinodimethanes

Journal

SYNTHESIS-STUTTGART
Volume 46, Issue 13, Pages 1788-1792

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1341238

Keywords

o-quinodimethane; Diels-Alder reaction; 1,4-elimination; silicon; mesylate; fluoride

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2-[(Trimethylsilyl)methyl]benzyl methanesulfonates react with potassium fluoride in the presence of a catalytic amount of 18-crown-6 at room temperature to give o-quinodimethanes, which are trapped with electron-deficient olefins to afford [4+2] cycloadducts in good yields.

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