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Phase transfer agents. II. Stereospecific hydroxylation of oleyl and elaidyl alcohol and periodic acid cleavage of epoxides
Author(s) -
Okimoto Tomoyuki,
Swern Daniel
Publication year - 1977
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02909057
Subject(s) - potassium permanganate , chemistry , hydroxylation , methylene , oleyl alcohol , chloride , stereospecificity , alcohol , aqueous solution , permanganate , aqueous two phase system , organic chemistry , medicinal chemistry , catalysis , enzyme
and Summary Oleyl and elaidyl alcohol have been stereospecifically hydroxylated by cold, dilute alkaline potassium permanganate to erythro ‐ and threo ‐9,10‐dihydroxyoctadecanol, respectively, in 40–80% yields in a water‐methylene chloride heterogeneous system. Phase transfer agents (PTA) were used to transport permanganate ion from the aqueous to the organic phase. In the absence of PTA, hydroxylation did not take place. Periodic acid cleavage of epoxides in a water‐methylene chloride system was studied in the absence and presence of PTA. At slow stirring rates PTA exert a rate accelerating effect in cleaving certain epoxides to aldehydes but with vigorous stirring use of PTA has only a marginal advantage.