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Catalytic deuteration of alkynols and their tetrahydropyranyl ethers
Author(s) -
Rakoff Henry,
Rohwedder William K.
Publication year - 1992
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02536142
Subject(s) - catalysis , chemistry , deuterium , hydrogen , triphenylphosphine , medicinal chemistry , organic chemistry , salt (chemistry) , physics , quantum mechanics
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 d 4 (using Wilkinson's catalyst, tris (triphenylphosphine)‐chlororhodium) or percent d 2 (using Lindlar's catalyst, Pd on CaCO 3 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 d 4 . This scatter was not observed with the corresponding THP ethers.