Pyridine is an organocatalyst for the reductive ozonolysis of alkenes

Rachel Willand-Charnley; Thomas J. Fisher; Bradley M. Johnson; Patrick H. Dussault

doi:10.1021/ol300617r

Pyridine is an organocatalyst for the reductive ozonolysis of alkenes

Rachel Willand-Charnley, Thomas J. Fisher, Bradley M. Johnson, Patrick H. Dussault

Research output: Contribution to journal › Article › peer-review

80 Scopus citations

Abstract

Whereas the cleavage of alkenes by ozone typically generates peroxide intermediates that must be decomposed in an accompanying step, ozonolysis in the presence of pyridine directly generates ketones or aldehydes through a process that neither consumes pyridine nor generates any detectable peroxides. The reaction is hypothesized to involve nucleophile-promoted fragmentation of carbonyl oxides via formation of zwitterionic peroxyacetals.

Original language	English (US)
Pages (from-to)	2242-2245
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	9
DOIs	https://doi.org/10.1021/ol300617r
State	Published - May 4 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Pyridine is an organocatalyst for the reductive ozonolysis of alkenes",

abstract = "Whereas the cleavage of alkenes by ozone typically generates peroxide intermediates that must be decomposed in an accompanying step, ozonolysis in the presence of pyridine directly generates ketones or aldehydes through a process that neither consumes pyridine nor generates any detectable peroxides. The reaction is hypothesized to involve nucleophile-promoted fragmentation of carbonyl oxides via formation of zwitterionic peroxyacetals.",

author = "Rachel Willand-Charnley and Fisher, {Thomas J.} and Johnson, {Bradley M.} and Dussault, {Patrick H.}",

year = "2012",

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T1 - Pyridine is an organocatalyst for the reductive ozonolysis of alkenes

AU - Willand-Charnley, Rachel

AU - Fisher, Thomas J.

AU - Johnson, Bradley M.

AU - Dussault, Patrick H.

PY - 2012/5/4

Y1 - 2012/5/4

N2 - Whereas the cleavage of alkenes by ozone typically generates peroxide intermediates that must be decomposed in an accompanying step, ozonolysis in the presence of pyridine directly generates ketones or aldehydes through a process that neither consumes pyridine nor generates any detectable peroxides. The reaction is hypothesized to involve nucleophile-promoted fragmentation of carbonyl oxides via formation of zwitterionic peroxyacetals.

AB - Whereas the cleavage of alkenes by ozone typically generates peroxide intermediates that must be decomposed in an accompanying step, ozonolysis in the presence of pyridine directly generates ketones or aldehydes through a process that neither consumes pyridine nor generates any detectable peroxides. The reaction is hypothesized to involve nucleophile-promoted fragmentation of carbonyl oxides via formation of zwitterionic peroxyacetals.

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Pyridine is an organocatalyst for the reductive ozonolysis of alkenes

Abstract

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