Synthesis of /sup 13/C-labeled standards for use in coal liquefaction studies. II. Dissolving metal reactions applied to naphthalenes and indoles: effect of sonication
High yield syntheses of /sup 13/C-labeled standards for later use in coal liquefaction studies are described. An alternate route for the synthesis of 1-cyclohexanone-1-/sup 13/C is discussed. Naphthalene and 2,3-dimethylnaphthalene were reduced with metal-amine solutions. The effect of sonication on product distribution was investigated. The effect of different amine solvent and different metals also was studied. A series of indoles were reduced with lithium and ethylenediamine to study the effect of sonication. To aid identification of some reduction products, independent syntheses were conducted. Naphthalenol-1-/sup 13/C, phenol-1-/sup 13/C, 1-indanone-1-/sup 13/C, 3,4-dihydro-2(1H)-quinolinone-2-/sup 13/C, 1,2,3,4-tetrahydroquinoline-2-/sup 13/C and carbazole-9a-/sup 13/C were synthesized in good yield. The carbonation of 1,5-pentanedimagnesium bromide was shown to be a viable alternative route for the synthesis of 1-cyclohexanone-1-/sup 13/C. Sonication was found to be an efficient agitation method for the reductive dimerization or the reductive amination of naphthalene and 2,3-dimethylnaphthalene. The product distribution was found to be dependent on the selection of the amine solvent. Sodium was shown to be a better reagent for reductive dimerization than potassium, lithium, calcium, or magnesium. The synthesis of 6,6',7,7'-tetramethyl-,1'-binaphthyl, 6,6',7,7'-tetramethyl-1,2'-binaphthyl, 6,6',7,7'-tetramethyl-2,2'-binaphthyl and some of their hydro-derivatives are described. The reduction of indoles with lithium-ethylenediamine was found to be influenced by sonication which significant increased the yield of the 4,5,6,7-tetrahydro-derivative. N-Substituted indoles were shown to undergo reductive cleavage with lithium-ethylenediamine while being treated with ultrasound.
- Research Organization:
- Oklahoma State Univ., Stillwater (USA)
- OSTI ID:
- 6041657
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
010405 -- Coal
Lignite
& Peat-- Hydrogenation & Liquefaction
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400202* -- Isotope Effects
Isotope Exchange
& Isotope Separation
AROMATICS
AZAARENES
AZOLES
CARBON 13
CARBON ISOTOPES
COAL LIQUEFACTION
CONDENSED AROMATICS
EVEN-ODD NUCLEI
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
INDOLES
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
LIQUEFACTION
NAPHTHALENE
NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PYRROLES
STABLE ISOTOPES
STANDARDS
THERMOCHEMICAL PROCESSES