Abstract
Deprotonated 1-(benzotriazol-1-yl)propargyl ethyl ethers react with propargyl, allyl and alkyl bromides to give the expected substituted derivatives 2, 4 and 9, respectively. Subsequent eliminations of the benzotriazolyl group upon treatment with NaH or ZnBr
2
, and elaboration of the acetylene group, generate ethoxy substituted enediynes 3, 6, 8, dienynes 7 and enynes 12. Grignard reagents or LiAlH
4
convert 9 into α-ethoxy substituted alkynes 10 and 11.