Title: Adamantane
CAS Registry Number: 281-23-2
CAS Name: Tricyclo[3.3.1.13,7]decane
Synonyms: diamantane (obsolete)
Molecular Formula: C10H16
Molecular Weight: 136.23
Percent Composition: C 88.16%, H 11.84%
Literature References: Isoln from petroleum from Moravia province in Czechoslovakia: Landa, Machacek,
Collect. Czech. Chem. Commun. 3, 1 (1933); from American petroleum: Mair
et al., Anal. Chem. 31, 2082 (1959). Synthesis: Prelog, Seiwerth,
Ber. 74, 1769 (1941); Stetter
et al., Ber. 89, 1922 (1956); by aluminum chloride-catalyzed isomerization of tetrahydrodicyclopentadiene: Yan, Shreh,
Bull. Inst. Chem. Acad. Sinica Dec. 1965, no. 11, pp 79-81. Two step synthesis starting with dicyclopentadiene: Schleyer,
J. Am. Chem. Soc. 79, 3292 (1957); Schleyer, Donaldson,
ibid. 82, 4645 (1960); Ludwig
US 2937211 (1960 to du Pont).
Reviews: Stetter,
Angew. Chem. 66, 217 (1954); Fort, Schleyer,
Chem. Rev. 64, 277 (1964).
Properties: Crystallizes at -30°; can be purified by recrystallization from acetone or by sublimination. mp 269.6-270.8°.
Melting point: mp 269.6-270.8°
NOTE: The name diamantane has been abandoned as a synonym for adamantane and proposed as the name for the second member of the adamantane series, congressane: Vogl, Anderson,
Tetrahedron Lett. 1966, 415.
Use: The diamine as curing agent for epoxy resins [
US 3053907 (1962 to du Pont)].
