Personally, I find this very strange and adding to the amount of side ways looks the hemp chemistry industry has to endure.
That’s what I figured. Interesting that you observe closer to a 1:1 mixture of the 9S/9R diastereomers, and not the approximate 2:1 mixture Mechoulam saw when reducing d8. Reduction of d9 was reported as providing predominantly the 9R diastereomer in a 1:3 (S/R) ratio of products.
I guess taken together your findings sort of validates Mechoulam’s ratios, which I think were mentioned as about 2:1 and 1:3, respectively.
That’s what I’m seeing and I just wanted you to digress on the subject. The major benefit of the HHCs (and also d8) are their much better chemical stability due to their lack of doubly allylic/benzylic 10a position preventing any degradation initiated at 10a. Basically the underlying reason why d9 can be selectively be reduced to CBN in the presence of d8.
I think the discoloration observed in d8 is actually mostly from whatever little d9 is present and it contrasts better from the otherwise colorless bulk material.
Thanks for sharing the raw data which include a smaller chromatographic peak eluting just after the diastereomeric pair of HHCs. Any idea what that may be?