Baylis-Hillman mechanism: a new interpretation in aprotic solvents.
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.
Price
Kristin E
KE
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA.
Broadwater
Steven J
SJ
Jung
Hyun M
HM
McQuade
D Tyler
DT
D000179:Acrylates / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D007700:Kinetics; D010879:Piperazines / Q000737:chemistry; D012997:Solvents / Q000737:chemistry*
D000179:Acrylates; D000447:Aldehydes; D010879:Piperazines; D012997:Solvents; C007306:triethylenediamine