A B S T R A C T T h e proton ~~u c l e a r magnetic resonance (N.M.R.) spectra o f the four diastereoisomers o f camphane-2,3-diol are reported. T h e coupling constants between the 2-, 3-, and 4-protons agree with t h e values predicted byICarplus for ethane derivatives. In particular, the cis (0" dihedral angle) coupling constants (7.7 and 8.9 c.p.s.)
INTRODUCTIONIndirect spin-spin coupli~lg constants in substituted ethane clerivatives have attracted attention because of the depeizcleilce of their values on the dihedral angle between the CH bonds involved (1-7). The dilzedl-a1 angles are 60" and 180" in non-cyclic substiti~tecl ethanes, ~vhich, in general, exist in staggered rather than eclipsed forms. Tlzese are also the dihedral angles between vicinal C H bonds in six-membered rings existing in chair conforinations. I n each case the observed coupling constants may be weighted averages if more than one conformation exists to a n appreciable extent.Karplus (8) '~lfaaltz~script received iVovenrber 28, 1960.