The metal-ammonia reduction of mono- and dinaphthylbenzenes

Journal Article · Fri Jun 08 04:00:00 EDT 1990 · Journal of Organic Chemistry; (United States)

DOI:https://doi.org/10.1021/jo00299a023· OSTI ID:5891555

Marcinow, Z; Rabideau, P W ^[1]

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1. Indiana Univ.-Purdue Univ., Indianapolis (United States)

The metal-ammonia reduction of 1- and 2-phenylnaphthalene (9 and 10, respectively), 1,3-bis(1-naphthyl)benzene (5), 1,3-bis(2-naphthyl)benzene (6), 1,4-bis(1-naphthyl)benzene (7), and m-quinquephenyl (8) has been investigated. 9 affords a mixture of isomeric dihydro products together with 1-phenyl-1,2,3,4-tetrahydronaphthalene, and the effect of metal, temperature, and quenching methods on the product distribution is reported. 10 provided only a single dihydro (1,4-) isomer plus a tetrahydro product. Both 5 and 7 provided a number of dihydro, tetrahydro, hexahydro, and octahydro products. On the other hand, 6 afforded high yields of a single tetrahydro product with lithium, and exclusively an octahydro product when 5-7 mol of sodium was used. In contrast to the terphenyls, which seem to have a propensity for inner-ring reduction, none of the naphthyl benzenes showed any tendency to reduce in the central benzene ring. m-Quinquephenyl reduced in two rings with no evidence for reduction in the central or outer rings.

• OSTI ID: 5891555
• Journal Information: Journal of Organic Chemistry; (United States), Journal Name: Journal of Organic Chemistry; (United States) Vol. 55:12; ISSN JOCEA; ISSN 0022-3263
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKALI METALS
AMMONIA
AROMATICS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHROMATOGRAPHY
CONDENSED AROMATICS
ELEMENTS
GAS CHROMATOGRAPHY
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
ISOMERS
KINETICS
LITHIUM
METALS
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
ORGANIC COMPOUNDS
POLYPHENYLS
REACTION KINETICS
REDUCTION
SEPARATION PROCESSES
SODIUM
TEMPERATURE RANGE
TEMPERATURE RANGE 0065-0273 K
TERPHENYL-PARA
TERPHENYLS