Toluene → Diisopropylethylamine

Participants

Reaction Steps

Surprisingly, diisopropylethylamine in methylene chloride gave a 59:41 mixture of starting material:2-iodo product (Run #14), and only a trace of the 2-iodo product was observed in toluene under similar conditions. The low solubility of the hydrohalide salts of TMEDA, Et3N and Et2MeN in the above solvents may be responsible for their usefulness as opposed to the poor results with diisopropylethylamine. Precipitation of these hydrohalide salts may remove sufficient acid from the reaction so that the equilibrium is displaced toward product allowing the reaction to proceed to completion.

Provenance & Evidence