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

Hidenori Shirakawa, Hiroshi Sano*

*Department of Chemistry, Graduate School of Engineering, Gunma University, Tenjin 1-5-1, Kiryu, Gunma 376-8515, Japan, Email: sanogunma-u.ac.jp

H. Shirakawa, H. Sano, Synthesis, 2014, 46, 1788-1792.

DOI: 10.1055/s-0033-1341238 (free Supporting Information)


Abstract

2-[(Trimethylsilyl)methyl]benzyl methanesulfonates give o-quinodimethanes in the presence of potassium fluoride and a catalytic amount of 18-crown-6 at room temperature. A subsequent reaction with electron-deficient olefins affords [4+2] cycloadducts in good yields.

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proposed reaction pathway



Key Words

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


ID: J66-Y2014