8582 1 R = O B s , R'= D
R
2 2
R = D , R'=OBs
R=OAc R = H
prepared from norborneol-2-endo-dl' (0.99- 1.O d by combustion analysis), were solvolyzed (NaOAc buffer) under the conditions in Table I ; the 13C spectra of the Table I. *H Distribution by I3C Nmr in 3 from AcetolJsis of 1 and 2 Substrate (mmol)
Temp, "C
Time. hr
1 5 (2.25) 2a (4.24)
45 Reflux
24 20
-% D i n 3 (13%)C-1
C-2
C-6
46 38
46
11
38
22
a With tritiated analogs of 1 and 2 . average values for C-1, C-2. and C-6 of 40.1, 38.2, and 20.5 from 1. and 36.0. 37.7. and 25.6 from 2 were obtained.10n
norbornyl-d acetates clearly showed deuterium at C-1, C-2, and C-6 only; and integration gave the results in Table I. The total label scrambled to the remaining sites is known1° to be
