TY - JOUR
T1 - Base-initiated reformatsky condensations in the gas phase
AU - Castle, Lyle W.
AU - Hayes, Roger N.
AU - Gross, Michael L.
PY - 1990
Y1 - 1990
N2 - The ester enolate anion CH2=C(OEt)O- reacts with acetaldehyde and with acetone in the gas phase to produce 'stable' adducts that are amenable to study by collisional activation and tandem mass spectrometry (MS/MS). The activated adducts and deprotonated β-hydroxy ethyl ester reference ions both decompose by elimination of H2O, Et ̇, H2O followed by EtOH, and by a retro reaction to reform CH2=C(OEt)O-. The losses of H2O, Et *̇, and EtOH are assigned to be characteristic of a species of tetrahedral geometry. These losses are, however, attenuated for the ion-molecule adducts because, in addition to existing as tetrahedral complexes, they are also formed as ion-dipole and proton-bound species.
AB - The ester enolate anion CH2=C(OEt)O- reacts with acetaldehyde and with acetone in the gas phase to produce 'stable' adducts that are amenable to study by collisional activation and tandem mass spectrometry (MS/MS). The activated adducts and deprotonated β-hydroxy ethyl ester reference ions both decompose by elimination of H2O, Et ̇, H2O followed by EtOH, and by a retro reaction to reform CH2=C(OEt)O-. The losses of H2O, Et *̇, and EtOH are assigned to be characteristic of a species of tetrahedral geometry. These losses are, however, attenuated for the ion-molecule adducts because, in addition to existing as tetrahedral complexes, they are also formed as ion-dipole and proton-bound species.
UR - http://www.scopus.com/inward/record.url?scp=37049072724&partnerID=8YFLogxK
U2 - 10.1039/p29900000267
DO - 10.1039/p29900000267
M3 - Article
AN - SCOPUS:37049072724
SN - 1472-779X
SP - 267
EP - 271
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
IS - 2
ER -