Synthesis 2014; 46(13): 1788-1792
DOI: 10.1055/s-0033-1341238
paper
© Georg Thieme Verlag Stuttgart · New York

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

Hidenori Shirakawa
Department of Chemistry, Graduate School of Engineering, Gunma University, Tenjin 1-5-1, Kiryu, Gunma 376-8515, Japan   Fax: +81(277)301282   eMail: sano@gunma-u.ac.jp
,
Hiroshi Sano*
Department of Chemistry, Graduate School of Engineering, Gunma University, Tenjin 1-5-1, Kiryu, Gunma 376-8515, Japan   Fax: +81(277)301282   eMail: sano@gunma-u.ac.jp
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Publikationsverlauf

Received: 11. Februar 2014

Accepted after revision: 26. März 2014

Publikationsdatum:
13. Mai 2014 (online)


Abstract

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.

Supporting Information