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Pinacol rearrangement of jojoba bis‐epoxide
Author(s) -
Zeltser Inna,
Shani Ar
Publication year - 2002
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/s11746-002-0529-z
Subject(s) - epoxide , nucleophile , chemistry , yield (engineering) , medicinal chemistry , ring (chemistry) , amine gas treating , iodide , pinacol , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
Jojoba bis‐epoxide (1.6 mmol) undergoes pinacol rearrangement upon reaction with the iodide ion (60 mmol) under slightly acidic conditions, via an iodohydrin as an intermediate, to yield bis‐ketojojoba in high yield (92%) after 25 h reflux in THF; no hydroxy derivatives were detected. Since the nucleophilic opening of the epoxide ring is statistically equal on both sides, the rearranged product may have the two carbonyl groups on either side of the original carbon atoms of the two epoxide rings, both completely opened. MS of the rearranged products reveals that the ring opening is approximately equal on both sides of the epoxide ring. Other nucleophiles, such as acetate and amine, open the ring sluggishly without rearrangement.