Synthesis and Reactions of 3-(5-Dicyclopentadienyl)-1-Trimethylsilylpropyne

Abstract

3-(5-Dicyclopentadienyl)-l-trimethylsilylpropyne (DCPTSP) has been synthesized from endo-anti-5-chlorotricyclo [5.2.1.0 2 ' 6 ] deca-3, 8-diene (DCPC1) on reaction with l-trimethylsilylpropyne. This novel silylated tricyclic compound has been used to synthesize 1.4-bis (trimethylsilyl)-2,3-bis (5-dicyclopentadienylmethyl) 1,3-butadiene (TDCPMB) and 3-(5dicyclopentadienyl)-1-propyne (DCPP). Physical Methods:1 H and 13 C NMR spectra were recorded on a varian VXR-300 spectrometer using CDC1 3 as a solvent. Infra-red spectra were taken on a Perkin-Elmer 710B spectrophotometer. Elemental analyses were determined by Schwartzkopf Microanalytical Laboratory, Inc. Woodside, NY. Synthesis of 3-(5-dicyclopentadienyl)-l-trimethylsilylpropyne (DCPTSP)n-Butyllithium (48 ml, 0.12 mol) was placed in a one litre three necked round bottom flask equipped with a thermometer, a rubber septum, Brought to you by | Purdue University Libraries Authenticated Download Date | 5/31/15 2:04 AM