ScholarLens Back to search
2005•The Journal of Organic ChemistryRequires access

A New Interpretation of the Baylis−Hillman Mechanism

Kristin E. Price, Steven J. Broadwater, Brian Walker, D. Tyler McQuade

Open publisher page 209 citations

Abstract

[reaction: see text] On the basis of reaction rate data, we have proposed a new mechanism for the Baylis-Hillman reaction involving the formation of a hemiacetal intermediate. We have determined that the rate-determining step is second order in aldehyde and first order in DABCO and acrylate. We have shown that this mechanism is general to aryl aldehydes under polar, nonpolar, and protic conditions using both rate data and two isotope effect experiments.

About this research paper

What this paper is about

[reaction: see text] On the basis of reaction rate data, we have proposed a new mechanism for the Baylis-Hillman reaction involving the formation of a hemiacetal intermediate. We have determined that the rate-determining step is second order in aldehyde and first order in DABCO and acrylate. We have shown that this mechanism is general to aryl aldehydes under polar, nonpolar, and protic conditions using both rate data and two isotope effect experiments.

Why it matters

OpenAlex reports 209 citations for this work. Citation counts describe recorded attention and do not establish research quality.

Key contribution

A contribution statement is not available in the OpenAlex record.

Method / approach

Method details are not available in the OpenAlex metadata.

Main findings

Findings are not separately available in the OpenAlex metadata.

Limitations

Limitations are not available in the OpenAlex metadata.

Applications

Application details are not available in the OpenAlex metadata.

Available abstract

[reaction: see text] On the basis of reaction rate data, we have proposed a new mechanism for the Baylis-Hillman reaction involving the formation of a hemiacetal intermediate. We have determined that the rate-determining step is second order in aldehyde and first order in DABCO and acrylate. We have shown that this mechanism is general to aryl aldehydes under polar, nonpolar, and protic conditions using both rate data and two isotope effect experiments.

Key concepts: Chemistry, DABCO, Baylis–Hillman reaction, Hemiacetal, Aldehyde, Kinetic isotope effect, Mechanism (biology), Reaction mechanism

Related papers

Related paper 1Related paper 2Related paper 3
Back to paper searchBrowse research topicsOriginal source
A New Interpretation of the Baylis−Hillman Mechanism — Research Paper | ScholarLens