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B. (6 Equiv of l-Butynylcopper, 70-80°). The above reaction was repeated using III (5 g, 0.0131 mol), 1-butynylcopper (9.21 g, 0.079 mol), and pyridine (180 ml) in the indicated quantities. Separation as previously described and chromatography of the products on acid-washed alumina with Skellysolve B gave XXVIb (~0.47 g, 0.00154 mol, 12%) and then lib (a yellow oil, 1.92 g, 0.00827 mol, 63 %). The diacetylene exhibits infrared absorption at 4.47 µ (C=C), nuclear magnetic resonance at 8.8 (triplet, 3 H), 7.6 (quartet, 2 H), and 2.7 (multiplet, 3 H), and a parent mass spectral peak at 232.2.Diacetylene lib was converted to its monopicrate as follows.Solutions of picric acid (0.40 g, 0.00175 mol) and of lib (0.4 g, 0.00173 mol) in warm 95% ethanol (8 ml) were mixed. On standing orange needles of the monopicrate of lib precipitated (0.42 g, 9.1 X 10-1 mol, 53%), mp 133-134°( from 95% ethanol).

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