Jh. Ahn et al., A new method of synthesis for propargylic amines and ethers via benzotriazole derivatives using sodium dialkynyldiethylaluminates, J ORG CHEM, 64(2), 1999, pp. 488-492
1-(alpha-Aminoalkyl)benzotriazoles react with sodium dialkynyldiethylalumin
ates to give propargylic amines in excellent yields, including unsubstitute
d N,N-dialkyl propargylamines, which are difficult to obtain from Lithium a
cetylide. The reaction of alpha-benzotriazolyl alkyl ethers and sodium dial
kynyldiethylaluminate in the presence of zinc iodide also gives propargylic
ethers in excellent yields. Unsubstituted propargyl ethers are prepared vi
a the desilylation of trimethylsilylpropargyl ethers.