Barton's equatorial (e) bonds are admirably drawn so as to be antiparallel to the next-adjacent C-C bonds of the cyclohexane ring. But his polar (p) bonds (which we would call "axial") are off by about 30°, giving the carbon coordination a grossly non-tetrahedral appearance. The solid lines in this figure show the proper direction for the axial bonds. Anyone who draws such an erroneous structure for cyclohexane now, half a century after Barton's paper, will certainly not get the Nobel Prize for it - not even a satisfactory grade in elementary organic chemistry. |
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