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Baylis−Hillman Mechanism: A New Interpretation in Aprotic Solvents
Abstract
Using reaction rate data collected in aprotic solvents, we have determined that the Baylis-Hillman rate-determining step is second order in aldehyde and first order in DABCO and acrylate. On the basis of these data, we have proposed a new mechanism involving a hemiacetal intermediate. The proposed mechanism was then supported using two different kinetic isotope experiments.
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Citations
Cited by
Alternative energy input: mechanochemical, microwave and ultrasound-assisted organic synthesis
Baig, R. B. N., & Varma, R. S. (2012) · Chem. Soc. Rev. · doi:10.1039/c1cs15204a · Cited by 587
Plata, R. E., & Singleton, D. A. (2015) · Journal of the American Chemical Society · doi:10.1021/ja5111392 · Cited by 445
Gehring, T., Quaranta, M., Odell, B., Blackmond, D. G., & Brown, J. M. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201203398 · Cited by 99
Metadata
- Authors
- Price, K. E., Broadwater, S. J., Jung, H. M., & McQuade, D. T.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-12-14
- Volume
- 7
- Issue
- 1
- Pages
- 147-150
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2046662628
- Cited by
- 197
- References
- 0
- FWCI
- 7.63
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Baylis−Hillman Mechanism: A New Interpretation in Aprotic Solvents. https://app.cochat.ai/papers/10.1021/ol047739o
- The paper
- Price, K. E., Broadwater, S. J., Jung, H. M., & McQuade, D. T. (2005). Baylis−Hillman Mechanism: A New Interpretation in Aprotic Solvents. Organic Letters. https://doi.org/10.1021/ol047739o
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
