A new interpretation of the Baylis-Hillman mechanism.
[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.
Price
Kristin E
KE
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA.
Broadwater
Steven J
SJ
Walker
Brian J
BJ
McQuade
D Tyler
DT