A Facile and Efficient Method for the Rearrangement of Aryl-substituted Epoxides to Aldehydes and Ketones using Bismuth Triflate

Ram S. Mohan; Kaushik A. Bhatia; Kyle J. Eash; Nicholas M. Leonard; Matthew C. Oswald

A Facile and Efficient Method for the Rearrangement of Aryl-substituted Epoxides to Aldehydes and Ketones using Bismuth Triflate

Ram S. Mohan
, Kaushik A. Bhatia
, Kyle J. Eash
, Nicholas M. Leonard
, Matthew C. Oswald

Illinois Wesleyan University

Research output: Journal Article › Article › peer-review

Abstract

<div class="line" id="line-15"> Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01–0.1 mol% Bi(OTf)3•xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C&horbar;O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3•Et2O, currently used to effect epoxide rearrangements.</div>

Original language	American English
Journal	Tetrahedron Letters
Volume	42
State	Published - 2001

Keywords

Bismuth and compounds
epoxides
rearrangements.

Disciplines

Organic Chemistry

Access to Document

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Cite this

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title = "A Facile and Efficient Method for the Rearrangement of Aryl-substituted Epoxides to Aldehydes and Ketones using Bismuth Triflate",

abstract = " Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01\–0.1 mol\% Bi(OTf)3\•xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C\&horbar;O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3\•Et2O, currently used to effect epoxide rearrangements.",

keywords = "Bismuth and compounds, epoxides, rearrangements.",

author = "Mohan, \{Ram S.\} and Bhatia, \{Kaushik A.\} and Eash, \{Kyle J.\} and Leonard, \{Nicholas M.\} and Oswald, \{Matthew C.\}",

year = "2001",

language = "American English",

volume = "42",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - A Facile and Efficient Method for the Rearrangement of Aryl-substituted Epoxides to Aldehydes and Ketones using Bismuth Triflate

AU - Mohan, Ram S.

AU - Bhatia, Kaushik A.

AU - Eash, Kyle J.

AU - Leonard, Nicholas M.

AU - Oswald, Matthew C.

PY - 2001

Y1 - 2001

N2 - Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01–0.1 mol% Bi(OTf)3•xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C&horbar;O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3•Et2O, currently used to effect epoxide rearrangements.

AB - Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01–0.1 mol% Bi(OTf)3•xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C&horbar;O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3•Et2O, currently used to effect epoxide rearrangements.

KW - Bismuth and compounds

KW - epoxides

KW - rearrangements.

M3 - Article

VL - 42

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -