Alkylation of acylmetalates with alkyl halides to prepare Fischer carbene complexes: an improved protocol |
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Authors: | Bappaditya NandiSurajit Sinha |
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Institution: | Department of Organic Chemistry, Indian Association for the Cultivation of Science, Kolkata 700032, West Bengal, India |
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Abstract: | Alkoxy Fischer carbene complexes have been synthesized by alkylation of lithium acylmetalates with alkyl halides in the presence of catalytic amount (5-10 mol %) of n-tetrabutylammonium bromide (n-Bu4NBr) restricting the temperature below 55 °C to minimize decomposition of the product. The reaction occurs in a biphasic condition involving water and alkyl halide. The effect of cesium on this alkylation reaction has been studied. The presence of a radical quencher, di-tert-butyl phenol, neither affects the yield nor leads to the formation of dimer of di-tert-butyl phenol, which rules out the possibility of radical pathway mechanism. The kinetic study and the 1H NMR spectra of products suggest an SN2 pathway particularly involving alkyl halides. |
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Keywords: | Fischer carbene complex Alkylation Cesium carbonate Mechanistic study |
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