Tetrahedron letters

An exceptionally simple and efficient synthesis of 6-methyl-6-vinylfulvene, and its oxidative transformations

I Erden, C Gärtner

Index: Erden, Ihsan; Gaertner, Christian Tetrahedron Letters, 2009 , vol. 50, # 20 p. 2381 - 2383

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Citation Number: 9

Abstract

A new efficient synthesis of 6-methyl-6-vinylfulvene was developed, starting from the 6-(2- hydroxyethyl)-6-methylfulvene. With larger quantities of the title compound in hand, its photooxygenation with singlet oxygen was studied. Cyclization of the cyclopropanone intermediate to both vinyl moieties in the unsaturated system was observed, whereas the saturated endoperoxide gave mostly the cyclopentenone derivative. m-CPBA attacks ...