Abstract
“Skipped” (1,4-) diynes have been prepared by coupling alkynyl Grignard reagents with propargyl bromides. Treatment with base isomerizes the 1,4- to conjugated 1,3-diynes. Two alleged routes to 1,5-diphenyl-1,4-pentadiyne have now been shown to give 1,4-diphenylbutadiyne. Spectral properties, NMR, IR, UV, are given for both series. Shoolery's rule is found useful in predicting the chemical shift, τ(CH 2),for these and other kinds of acetylenic compounds. On the basis of their UV spectra, one can say that in the 1,4-diynes there is little, if any, conjugation “through” the internal methylene group, and what conjugation there is, is less than that in 1,3-diynes.
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