Tetrahedron

The intermediacy of oxycyclobutenes in the synthesis and reactions of cyclobutenones and cyclobutenols

AA Frimer, H Pizem

Index: Frimer, Aryeh A.; Pizem, Hillel Tetrahedron, 1999 , vol. 55, # 41 p. 12175 - 12186

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Citation Number: 5

Abstract

Vinylcyclobutenol 7, generated via the singlet oxygenation of alkylidenecyclobutene 5, rearranges at room temperature to a solvent dependent mixture of isomeric dienones 10 and 11. Alkylidenecyclobutene 5 was prepared in turn via an inverse Wittig addition of the isopropyl ylide to cyclobutenone 4; in a normal addition of ketone to ylide, vinylallene 12 is also obtained. Finally, the corresponding Wittig reaction of 4, 4-dichlorocyclobutenone 3 ...