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The mass spectra of acetylenic ketones and their secondary amine adducts
Author(s) -
Aplin R. T.,
Mestres R.
Publication year - 1970
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.1210030811
Subject(s) - chemistry , ketone , mass spectrum , aryl , alkyl , adduct , morpholine , amine gas treating , medicinal chemistry , ion , stereochemistry , organic chemistry
The mass spectra of a number of alkyl and aryl acetylenic ketones of the type RCO·CC·CC·R′ have been examined. All the spectra exhibit molecular ions together with the expected intense fragments arising from cleavage α‐to the carbonyl group. The most striking feature of the ketone spectra is the loss of CO from the molecular ion. This process dominates the spectra of the aryl ketones, the spectra below [M – 28]+˙. being virtually identical to those of the corresponding phenylacetylenes. The spectra of the piperidene and/or morpholine adducts of the alkyl ketones are very similar to those of the parent ketone whereas those of the aryl ketones are dominated by the loss HO˙ from the molecular ion. Deuterium labelling has established the site of the hydrogen involved as being the carbons α‐ to the nitrogen of the heterocyclic ring.