Bismuth(III) Oxide Perchlorate Promoted Rearrangement of Epoxides to Aldehydes and Ketones

Ram S. Mohan; Andrew M. Anderson; Jesse M. Blazek; Parie Garg; Brian J. Payne

Bismuth(III) Oxide Perchlorate Promoted Rearrangement of Epoxides to Aldehydes and Ketones

Ram S. Mohan, Andrew M. Anderson, Jesse M. Blazek, Parie Garg, Brian J. Payne

Illinois Wesleyan University

Research output: Journal Article › Article › peer-review

Abstract

<div class="line" id="line-15"> 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•xH2O, to give carbonyl compounds. The rearrangement is regioselective with aryl substituted epoxides and a single carbonyl compound arising from cleavage of benzylic C&horbar;O bond is formed. BiOClO4•xH2O 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.</div>

Original language	American English
Journal	Tetrahedron Letters
Volume	41
State	Published - 2000

Disciplines

Organic Chemistry

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Cite this

@article{cd76873123254d26a9c9e013596adfea,

title = "Bismuth(III) Oxide Perchlorate Promoted Rearrangement of Epoxides to Aldehydes and Ketones",

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\•xH2O, to give carbonyl compounds. The rearrangement is regioselective with aryl substituted epoxides and a single carbonyl compound arising from cleavage of benzylic C\&horbar;O bond is formed. BiOClO4\•xH2O 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.",

author = "Mohan, \{Ram S.\} and Anderson, \{Andrew M.\} and Blazek, \{Jesse M.\} and Parie Garg and Payne, \{Brian J.\}",

year = "2000",

language = "American English",

volume = "41",

journal = "Tetrahedron Letters",

}

TY - JOUR

T1 - Bismuth(III) Oxide Perchlorate Promoted Rearrangement of Epoxides to Aldehydes and Ketones

AU - Mohan, Ram S.

AU - Anderson, Andrew M.

AU - Blazek, Jesse M.

AU - Garg, Parie

AU - Payne, Brian J.

PY - 2000

Y1 - 2000

N2 - 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•xH2O, to give carbonyl compounds. The rearrangement is regioselective with aryl substituted epoxides and a single carbonyl compound arising from cleavage of benzylic C&horbar;O bond is formed. BiOClO4•xH2O 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.

AB - 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•xH2O, to give carbonyl compounds. The rearrangement is regioselective with aryl substituted epoxides and a single carbonyl compound arising from cleavage of benzylic C&horbar;O bond is formed. BiOClO4•xH2O 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.

M3 - Article

VL - 41

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -