Stereospecific Alcohol Elimination From Dialkyl Mesaconates Under Electron Impact: Another Example of a Hidden Hydrogen Transfer

Article abstract of DOI:10.1002/oms.1210210410

Under electron impact dimethyl and diethyl mesaconates give rise to abundant ^+. and < M - EtOH>^+. ions, respectively.The geometrically isomeric citraconates yield ^+. and ^+. ions.Mixed methyl ethyl mesaconates eliminate both methanol and ethanol.These findings, together with the results of a deuterium labelling study, indicate that the elimination of alcohol from the molecular ions of the mesaconates is partially preceded by a hidden hydrogen transfer step.