NISTC10024187

Bromoallene is used as a useful reagent for synthesis of terminal alkynic compounds and substituted allenes.

A tedious preparation5 of bromoallene by isomerization of propargyl bromide in the presence of copper(I) bromide has been improved6 and pure bromoallene can be obtained by removing the side product (propargyl bromide) with diethylamine (eq 1). Bromoallene has also been prepared by flash vacuum pyrolysis of bromocyclopropene4 or by phase transfer catalysis using CHBr(CH2Br2),7 but in both cases reaction mixtures contained a significant amount of propargyl bromide.

Journal of the American Chemical Society, 75, p. 1314, 1953 DOI: 10.1021/ja01102a014
Synthetic Communications, 21, p. 69, 1991 DOI: 10.1080/00397919108020791