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Abstract
The title compound, C16H22Cl2O, was synthesized from β-himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The molecule is built up from fused six- and seven-membered rings and an additional three-membered ring arising from the reaction of himachalene with dichlorocarbene. The six-membered ring has an envelope conformation, with the C atom belonging to the three-membered ring forming the flap, whereas the seven-membered ring displays a screw-boat conformation; the dihedral angle between the rings (all atoms) is 59.65 (14)°.
Highlights
The title compound, C16H22Cl2O, was synthesized from himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1Hbenzocycloheptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica)
The molecule is built up from fused six- and seven-membered rings and an additional three-membered ring arising from the reaction of himachalene with dichlorocarbene
The six-membered ring has an envelope conformation, with the C atom belonging to the three-membered ring forming the flap, whereas the sevenmembered ring displays a screw-boat conformation; the dihedral angle between the rings is 59.65 (14)
Summary
Naja Ourhriss,a Ahmed Benharref,a Abdelouahd Oukhrib,a Jean-Claude Daranb and Moha Berrahoa*. The title compound, C16H22Cl2O, was synthesized from himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1Hbenzocycloheptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The molecule is built up from fused six- and seven-membered rings and an additional three-membered ring arising from the reaction of himachalene with dichlorocarbene. Related literature For background to the essential oil of the Alas cedar (Cedrus atlantica), see: Joseph & Dev (1968); Plattier & Teiseire (1974). For the reactivity and biological properties of himachalene, see: Benharref et al (2012); Chekroun et al (2000); El Jamili et al (2002); Lassaba et al (1998); Dakir et al (2004); Daoubi et al (2004). See: Cremer & Pople (1975)
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