ISSN:
1573-9171
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary 1. Deutero-2,4,-dimethyl- Δ2 -cyclopenten-1-one was obtained by the cyclization of 2-methylhexadien-3-one in the presence of deuterium enriched phosphoric acid. 2. When deutero-2,4-dimethyl- Δ2 -cyclopenten-1-one was ozonized, methylsuccinic acid was obtained which contained almost all the initial deuterium of the dimethylcyclopentenone. This excludes the presence of deuterium at carbon atoms 1,2,3 or 6 in the molecule of deutero-2,4-dimethyl- Δ2-cyclopenten-1-one. 3. Oxidation of deutero-2,4-dimethyl- Δ2 -cyclopenten-1-one with seleniumdioxide gave 2,4-dimethyl-cyclopenten-1,5-dione containing no deuterium. From this it follows that the deuterium in deutero-2,4-dimethyl Δ2 -cyclopenten-1-one occurs at carbon 5, i.e., at the methylene group adjacent to the carbonyl. 4. This position nf deuterium in deutero-2,4-dimethyl- Δ2-cyclopontenone shows that it is not isopropenylallyl-ketone (2-methyl-1,5-hexadien-3-one) (I) but its isomer, 2-methyl-1,4-hexadien-3-one (IV) that is cyclized.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01171522
Permalink