I 2-iodophenyl acetylide

A 1-L flask is charged with the copper(I) (2-iodophenyl)acetylide (17.9 g, 0.0616 mol) and placed under an active vacuum to remove remaining volatiles and effect constant weight (ca. 18 h at 10 4 torr). About 500 mL of 

Copper(I) (2-iodophenyl)acetylide exhibits a stronger CsC stretch at 1935 cm-1 in the IR spectrum. 

Tribenzocyclyne is a bright yellow solid which decomposes at 215-220°C. The H NMR spectrum (CDC13) exhibits multiplets centered at 7.32 (6H) and 7.17 S (6H) typical of an AA BB spin system. The 13C NMR spectrum (CDC13) exhibits peaks at 132.0, 128.6, 126.7, and 92.9 6. A very weak CsC stretch is observed at 2217 cm-1 in the IR spectrum. Mass spectroscopic evidence indicates a parent ion at m/e = 300. 

We would like to thank Dr. Michael J. Taschner for helpful discussions. C. A. T. and W. J. Y. would like to thank the Petroleum Research Fund, Office of Naval Research, State of Ohio through the Edison Center for Sensors and Technology at CWRU, and the National Science Foundation for supporting different aspects of this research. 

Nakagawa, The Chemistry of the Carbon-Carbon Triple Bond, Part 2, S. Patai, (ed.) Wiley Chichester, 1978, pp. 635-712. 

Tetrabenzocyclyne is a colorless solid which decomposes at 220°C. An AA BB spin system is again observed in the H NMR spectrum (CDCI3) where QBC exhibits multiplets centered at 7.53 (8H) and 7.26 5 (8H). The NMR (CDCI3) exhibits peaks at 132.3, 128.0, 125.6, and 91.1 5. A very weak CsC stretch is observed at 2214cm in the IR spectrum. Mass spectroscopic evidence for QBC includes an M ion at m/z = 400, a peak corresponding to the loss of acetylene at mjz = 374, and a doubly charged M ion at mjz = 200. 

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Caution. When dry, copper acetylides are known to be shock and thermally sensitive. Copper (I) (2-iodophenyl)acetylide should therefore be handled with care. 

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