Competition between birch reduction and bond cleavage in 1,2-bis(4-methyl-1-naphthyl)ethane
- Indiana Univ.-Purdue Univ., Indianapolis (USA)
The reaction of 1,2-bis(4-methyl-1-naphthyl)ethane with Li, Na, and K in ammonia, THF, and HMPA, or mixtures thereof, has been examined with respect to the factors favoring Birch reduction of the aromatic ring and cleavage of the ethane carbon-carbon bond. Bond cleavage was found to increase relative to ring reduction in the series Li < Na < K and with the solvents NH{sub 3} < THF < HMPA. However, the latter position of ammonia may be due to the necessarily restricted low-reaction temperature since only ring reduction was observed at temperatures at or below the boiling point of ammonia (-33{degree}C). A number of reduction and cleavage products were isolated and identified, and the mechanistic pathways for their formation is discussed.
- OSTI ID:
- 7071576
- Journal Information:
- Journal of Organic Chemistry; (USA), Journal Name: Journal of Organic Chemistry; (USA) Vol. 54:15; ISSN 0022-3263; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ALKALI METALS
ALKANES
AMMONIA
AROMATICS
BONDING
CHEMICAL REACTIONS
DATA
DATA ANALYSIS
ELEMENTS
ETHANE
EXPERIMENTAL DATA
FABRICATION
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
INFORMATION
JOINING
LITHIUM
MEASURING INSTRUMENTS
MEASURING METHODS
METALS
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NUMERICAL DATA
ORGANIC COMPOUNDS
POTASSIUM
REDUCTION
SODIUM