A TRICYCLIC TERPENE HYDROCARBON - CYCLOPINENE

Article abstract of DOI:10.1007/BF00579419

The reduction of the tosylate of filipendulol (2,7,7-trimethylbicyclo<3.1.1>hept-2-en-6-ol) with lithium tetrahydroaluminate in ether has given a hydrocarbon (I), C10H16 (bp 66.5 deg C/50 mm, n²⁰_D 1.4565, d²⁰₂₀ 0.8599, <α>¹⁹_D -104.5 deg.NMR: 0.69 ppm (CH3); 0.95 ppm, (CH3); 1.17 ppm (CH3); no signals of olefinic protons.IR: 3054 cm^-1 (three-membered ring with gem-protons); 1363 and 1387 cm^-1 (gem-CH3), absorption bands of multiple bonds absent.Heating (70 deg C) (I) with a sulfonated cation-exchange resin in hexane gave α-pinene.The hydrogenation of (I) over PtO2 in acetic acid gave pinane.The most probable structure of (I) is 2,7,7-trimethyltricyclo<3.1.1.0^2,4>heptane.The substance has been called cyclopinene.