Synthesis and reactivity of new strained cyclic allene and alkyne precursors

Abstract

The synthesis of ortho-(trimethylsilyl)vinyl inflates 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. © 2006 IUPAC.