Catalytic deuteration of alkynols and their tetrahydropyranyl ethers
1992
Rakoff, H. | Rohwedder, W.K.
To ascertain the effect of a replaceable hydrogen on deuterium incorporation, 2-pentynol, 2-hexynol, 3-hexynol, their tetrahydropyranyl (THP) ethers, and the mono- and di-THP ethers of 3-hexyne-1,6-diol were deuterated catalytically with deuterium gas. The differences in percent d4 (using Wilkinson's catalyst, tris(triphenylphosphine)-chlororhodium) or percent d2 (using Lindlar's catalyst, Pd on CaCO3 poisoned with a lead salt) measured for the alcohols and their THP ethers were, in general, less than 4% with either catalyst. Noticeable exceptions occurred during the deuteration over Wilkinson's catalyst of 2-pentynol and 2-hexynol; extensive scatter resulted in a substantial decrease in percent d4. This scatter was not observed with the corresponding THP ethers.
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