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Mechanism of enolic ion tautomerization
Author(s) -
Eadon George
Publication year - 1973
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210071207
Subject(s) - tautomer , chemistry , deuterium , ion , transition state , mass spectrum , photochemistry , hydrogen , ring (chemistry) , mechanism (biology) , computational chemistry , medicinal chemistry , atomic physics , catalysis , physics , organic chemistry , quantum mechanics
Evidence of enolic ion‐enolic ion tautomerization was observed in the mass spectra of several alkylcyclobutanols and aliphatic ketones. Extensive deuterium labeling experiments on 1‐butylcyclobutanol, 5‐nonanone and 7‐tridecanone demonstrated that the process did not involve the intermediacy of the ketonic ion. The predominant mechanism involves reciprocal hydrogen transfers through large ring transition states, rather than a direct 1,3 hydrogen shift. Other decomposition reactions of the enolic ions were observed.