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Dissolving metal reduction of aceanthrylene and NMR analysis of a rigid, boat-shaped 9,10-dihydroanthracene

Journal Article · · J. Org. Chem.; (United States)
DOI:https://doi.org/10.1021/jo00238a020· OSTI ID:5993176
; ; ;

Aceanthrylene is reduced by sodium/ammonia solution to its 2,6-dihydro derivative (4), which indicates a protonation site in the dianion in contrast to the MNDO-calculated position of highest electron density. It is concluded that monoanion stability must be the prevailing feature. Compound 4 is also reduced by sodium/ammonia to provide 1,9-ethano-9,10-dihydroanthracene, which allowed the first proton NMR study of a rigid, boat-shaped dihydroanthracene. Especially interesting are the long range, five-bond homoallylic couplings between the 9- and 10-positions, and the values measured are 4.7 Hz for /sup 5/J/sub 9,10/ (dipseudoaxial) and 1.4 Hz for /sup 5/J/sub 9,10'/ (pseudoaxial/pseudoequatorial). The protonation and alkylation of (3-phenylindenyl)lithium is also considered so as to better understand the behavior of the intermediates derived from aceanthrylene. 20 references, 3 tables.

Research Organization:
Indiana Univ., Indianapolis (USA)
OSTI ID:
5993176
Journal Information:
J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 53:3; ISSN JOCEA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
400202 -- Isotope Effects
Isotope Exchange
& Isotope Separation
ALKALI METALS
AMMONIA
ANTHRACENE
AROMATICS
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
CONDENSED AROMATICS
DATA
DEUTERIUM
ELEMENTS
EXPERIMENTAL DATA
HALOGENATED ALIPHATIC HYDROCARBONS
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
INFORMATION
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
MAGNETIC RESONANCE
METALS
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
RESONANCE
SODIUM
SOLVENT PROPERTIES
STABLE ISOTOPES