Dickman, John published the artcileMass spectrometry in structural and stereochemical problems. CLXIX. Determination of the structures of the ions produced in the single and double McLafferty rearrangements by ion cyclotron resonance spectroscopy, Category: alcohols-buliding-blocks, the publication is Journal of the American Chemical Society (1969), 91(8), 2069-84, database is CAplus.
Two possible structural isomers of the C3H6O•+ ion produced by electron impact induced fragmentations are the keto ion Me2CO+• and the enol ion MeC(:CH2)O+H•. The electron impact induced double Mc-Lafferty rearrangement can also produce a C3H6O•+ ion which could conceivably exist in either the enol or sym. oxonium ion structure. Ion cyclotron resonance and pulsed double resonance spectroscopy are used to study the ion-mol. reactions of the keto species, generated from acetone; the enol species, generated from 2-hexanone (via a McLafferty rearrangement) and from 1-methylcyclobutanol; and the double McLafferty species, generated from 5-nonanone. Seven ion-mol. reactions are found which distinguish between the keto and enol ions, thus substantiating the proposed differences in structure. In all cases studied, the enol ion, from 2-hexanone and the enol ion from 1-methylcyclobutanol behave identically indicating their structures to be equivalent The same ion-mol. reactions which distinguish between the keto and enol isomers can be utilized to distinguish between the keto and double McLafferty species. The enol and double McLafferty species react identically in all systems studied thus suggesting identical structures and raising serious doubts about the earlier proposed existence of a sym. double McLafferty oxonium ion. Deuterium labeling is employed to distinguish between isomeric ions of identical mass.
Journal of the American Chemical Society published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Category: alcohols-buliding-blocks.
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