The Synthesis and Photoisomerization of 5??Methyl??5??Vinyl??1, 3??Cyclopentadiene

…, E Pamingle??Cristoforetti, AO Bringhen

Index: Burger, Ulrich; Pamingle-Cristoforetti, Eliane; Bringhen, Alain O. Helvetica Chimica Acta, 1988 , vol. 71, p. 389 - 394

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Abstract

Abstract A versatile scheme for the synthesis of geminally disubstituted cyclopentadienes is used to prepare the title compound 4. This remarkably stable vinyl-cyclopentadiene, distinguished by its C s symmetry, undergoes exclusively electrocyclic ring closure upon direct π–π* excitation at 254 nm. The epimeric vinyl-housenes 11 and 12, which, for geometric reasons, are insensitive to the walk rearrangement, are suggested to be the ...