The Effect of Alkyllithium Reagent on Alkylation of Mono- and Disubstituted Vinyl Bromides via Halogen-Metal Exchange

References

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• Glpc yields were obtained on a Varian Aerograph Model 600-D gas chromatograph using a 20% SF-96 on chromsorb Q stainless steel column (1/8″ × 5′) and were determined by comparing the integrations of the product peak against an internal standard peak (undecane - Table I; dodecane - Table II) following flame factor corrections
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• Halogen-metal exchange was carried out at -78oC in tetrahydrofuran solvent. Alkylation was carried out by addition of 2 equivalents of ethyl iodide at -78oC and maintaining the mixture at this temperature for 15 min before warming to room temperature and stirring an additional 2h
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• The halogen-metal exchange reaction was carried out as with the disubstituted vinyl bromides (tetrahydrofuran solvent at -78oC) but the alkylation times varied. In all cases, addition of ethyl iodide was carried out at -78oC and the mixture maintained at this temperature for 15 min before warming to room temperature; then in the first and fifth entries in Table II the reaction was allowed to proceed an additional 6h, while for the rest of the entries the the reaction only continued for an additional Ih
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