4380
N E A U B R E YA N D J. R. VAN WAZER
o/ '
1'01. h(j
1-ethriq.l-c2's-~-t-butylc~clohexaiiol and 1 -eth~-~lyl-trun.s4-t-butylcyclohexanol are 690 and lO(i0 c.p.s. SlioIi respectively. This phenomenon is currently being investigated for the purpose of determining whether the slope of the concentration-chemical shift relatioriship can be useful in confirming and assigning stereochemistry.
H
Experimental Fig. 2.-DitiietIiyl
sulfoxide &-it11c.is-4-t-butylcyclohexanol
I t is interesting to note that not only is the chemical shift of the hydroxyl proton a function of stereochemistry, but the slope of the line relating the chemical shift with concentration in carbon tetrachloride is also. As was previously pointed out,'O one would expect the hydroxyl group in the axial position to be less hydrogen bonded than in the equatorial position In the axial position the hydroxyl group can probably be bonded best with the hydrogen directly away from the plane of the ring. The slopes for cis-l-t-butylare 25 1 0 cyclohexanol and trans-4-f-butylcyclohexanol and 3160 c.p.s.~'l\7~
