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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 451-455

Synthesis and reactivity of new strained cyclic allene and alkyne precursors

Diego Peña, Beatriz Iglesias, Iago Quintana, Dolores Pérez, Enrique Guitián and Luis Castedo

Departamento de Química Orgánica, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain

Abstract: The synthesis of ortho-(trimethylsilyl)vinyl triflates is described. Fluoride-induced decomposition of these triflates leads to the generation of strained cycloallenes and cycloalkynes under mild reaction conditions. The generation rate of these highly reactive intermediates can be modulated by modifying the solubility of the fluoride source. The slow generation of cyclic allenes and alkynes is a prerequisite for their use in homogeneous catalysis.