Bismuth(III) oxide perchlorate promoted rearrangement of epoxides to aldehydes and ketones
Date
2012-11-14
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Abstract
Aryl-substituted epoxides and aliphatic epoxides with a tertiary epoxide carbon undergo smooth rearrangement
in the presence of 10–50 mol% bismuth(III) oxide perchlorate, BiOClO4 H2O, to give carbonyl compounds.
The rearrangement is regioselective with aryl substituted epoxides and a single carbonyl compound arising
from cleavage of benzylic C–O bond is formed. BiOClO4 H2O is relatively non-toxic, insensitive to air and
inexpensive, making this catalyst an attractive alternative to more corrosive and toxic Lewis acids such as BF3 Et2O
or InCl3 currently used to effect epoxide rearrangements. © 2000 Elsevier Science Ltd. All rights reserved
Description
Aryl-substituted epoxides and aliphatic epoxides with a tertiary epoxide carbon undergo smooth rearrangement
in the presence of 10–50 mol% bismuth(III) oxide perchlorate, BiOClO4 H2O, to give carbonyl compounds.
The rearrangement is regioselective with aryl substituted epoxides and a single carbonyl compound arising
from cleavage of benzylic C–O bond is formed. BiOClO4 H2O is relatively non-toxic, insensitive to air and
inexpensive, making this catalyst an attractive alternative to more corrosive and toxic Lewis acids such as BF3 Et2O
or InCl3 currently used to effect epoxide rearrangements. © 2000 Elsevier Science Ltd. All rights reserved
Keywords
bismuth; bismuth compounds; epoxides; rearrangements.