Methoxybenzo(a)pyrene 4,5-oxides labeled with carbon-13: electronic effects in the NIH shift
Journal Article
·
· J. Org. Chem.; (United States)
The synthesis of 9-methoxy-4,5-dihydrobenzo(a)pyrene-4-/sup 13/C 4,5-oxide and -5-/sup 13/C 4,5-oxide and of 8-methoxy-4,5-dihydrobenzo(a)pyrene-4-/sup 13/C 4,5-oxide is reported. The compounds were synthesized in yields of 15% each from unlabeled precursors. /sup 1/numberC NMR analysis of the conversion of the 4,5-oxides to 4-phenols and 5-phenols (NIH shift) revealed a very strong electronic effect of a 9-methoxy substituent, which gave only the 4-phenol, and a significant but weaker effect of an 8-methoxy substituent, which gave both phenols with the 5-phenol predominating. 18 references, 3 figures, 1 table.
- Research Organization:
- Univ. of New Mexico, Albuquerque
- OSTI ID:
- 6036629
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 50:26; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
AROMATICS
CARBON 13
CARBON ISOTOPES
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHALCOGENIDES
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CONDENSED AROMATICS
DATA
EVEN-ODD NUCLEI
EXPERIMENTAL DATA
HYDROCARBONS
INFORMATION
ISOMERIZATION
ISOTOPES
LABELLING
LIGHT NUCLEI
MAGNETIC RESONANCE
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PH VALUE
PYRENE
RESONANCE
SPECTRA
STABLE ISOTOPES
SULFONIC ACIDS
SYNTHESIS
YIELDS
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
AROMATICS
CARBON 13
CARBON ISOTOPES
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHALCOGENIDES
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CONDENSED AROMATICS
DATA
EVEN-ODD NUCLEI
EXPERIMENTAL DATA
HYDROCARBONS
INFORMATION
ISOMERIZATION
ISOTOPES
LABELLING
LIGHT NUCLEI
MAGNETIC RESONANCE
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PH VALUE
PYRENE
RESONANCE
SPECTRA
STABLE ISOTOPES
SULFONIC ACIDS
SYNTHESIS
YIELDS