Abstract
The title compound, C16H24Cl2O, was synthesized by treating (1S,3R,8S,9R,10S)-2,2-di-chloro-3,7,7,10-tetra-methyl-9,10-ep-oxy-tri-cyclo-[6.4.0.0(1,3)]dodecane with a concentrated solution of hydro-bromic acid. It is built up from three fused rings: a cyclo-heptane ring, a cyclo-hexyl ring bearing alkene and hy-droxy substituents, and a cyclo-propane ring bearing two chlorine atoms. The asymmetric unit contains two mol-ecules linked by an O-H⋯O hydrogen bond. In the crystal, further O-H⋯O hydrogen bonds build up an R 4 (4)(8) cyclic tetra-mer. One of the mol-ecules presents disorder that affects the seven-membered ring. In both mol-ecules, the six-membered rings display a chair conformation, whereas the seven-membered rings display conformations inter-mediate between boat and twist-boat for the non-disordered mol-ecule and either a chair or boat and twist-boat for the disordered mol-ecule owing to the disorder. The absolute configuration for both mol-ecules is 1S,3R,8R,9R and was deduced from the chemical pathway and further confirmed by the X-ray structural analysis.
Highlights
A cycloheptane ring, a cyclohexyl ring bearing alkene and hydroxy substituents, and a cyclopropane ring bearing two chlorine atoms
The asymmetric unit contains two molecules linked by an O—H O hydrogen bond
The six-membered rings display a chair conformation, whereas the seven-membered rings display conformations intermediate between boat and twist-boat for the non-disordered molecule and either a chair or boat and twistboat for the disordered molecule owing to the disorder
Summary
The main constituent (50%) of the essential oil of the Atlas cedar (Cedrus atlantica) is a bicyclic hydrocarbon sesquiterpene called -himachalene (Plattier & Teisseire, 1974; Joseph & Dev, 1968). The reactivity of this sesquiterpene and its derivatives has been studied extensively (Auhmani et al., 2002; El Jamili et al, 2002; Dakir et al, 2004). In order to prepare new optically active allylic alcohols using this sesquiterpene, we prepared the title compound (1S,3R,8R,9R)-2,2-dichloro-10methylene-3,7,7-trimethyltricyclo[6.4.0.01,3]dodecan-9-ol by treating (1S,3R,8S,9R,10S)-2,2-dichloro-3,7,7,10-tetramethyl9,10-epoxytricyclo[6.4.0.01,3]dodecane with a concentrated solution of hydrobromic acid
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