Multiple isomers of carbon(60)hydrogen(36): The products of the birch reduction of carbon(60)
Nossal, Jamie R.
Billups, W. Edward
Doctor of Philosophy
The product mixture of the lithium Birch reduction of C60 is analyzed. C60H36 is identified as the major product; C60H32, C60H38 and C60H 40 are identified as minor products. The product mixture is separated into four fractions by high pressure liquid chromatography. 3He NMR spectra are obtained for the fractions by reduction of 3He C 60 and the 3He chemical shifts are compared to calculated values. The dihydroanthracene reduction of C60 is shown by high pressure liquid chromatography to produce a single major isomer of C 60H36. A comparison of the 3He NMR spectra determines that the major dihydroanthracene C60H36 isomer has C3 symmetry and that this isomer is also obtained by the Birch reduction of C60. C60H38, C60H 40 and C60H42 are synthesized by the lithium-ethylenediamine reduction of C60H36. 1,2-C70H 2 is synthesized by anhydrous hydrazine reduction of C70.