Optimization of Allylic Oxidation of (1S,3R,8R)‐2,2‐Dichloro‐3,7,7,10‐tetramethyltricyclo[6,4,0,0 1,3 ]dodec‐9‐ene

The title compound, C16H24Br2, 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 two fused six- and seven-membered rings and an additional three-membered ring from the reaction of β-himachalene with dibromocarbene. The six-membered ring shows a screw-boat conformation, whereas the seven-membered ring displays a boat conformation; the dihedral angle between the mean planes through the rings is 57.9 (4)°. The absolute structure was established unambiguously from anomalous dispersion effects.

Section: Related Literaturementioning

confidence: 99%

Section: Commentmentioning

confidence: 99%

(1S,3R,8R)-2,2-Dibromo-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-9-ene

Benharref¹,

Ammari²,

Lassaba³

et al. 2012

“…For the reactivity of this sesquiterpene, see: Lassaba et al (1998); Chekroun et al (2000); El ; Sbai et al (2002); Dakir et al (2004). For its biological activity, see: Daoubi et al (2004).…”

Section: Related Literaturementioning

confidence: 99%

“…The reactivity of this sesquiterpene has been studied extensively by our team in order to prepare new products having biological proprieties (Lassaba et al, 1998;Chekroun et al, 2000;El Jamili et al, 2002;Sbai et al, 2002;Dakir et al, 2004). Indeed, these compounds were tested, using the food poisoning technique, for their potential antifungal activity against phytopathogen Botrytis cinerea (Daoubi et al, 2004).…”

Section: Commentmentioning

confidence: 99%

(1S,2R,8R)-2,2-Dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-10-en-9-one

Benharref¹,

Ammari²,

Berraho³

2010

The title compound, C16H22Cl2O, was synthesized from β-himachalene, which was isolated from essential oil of the Atlas cedar (cedrus atlantica). The asymmetric unit contains two independent molecules, in each of which the six-membered ring shows a half-chair conformation, whereas the seven-membered ring displays a boat conformation. The dihedral angle between the two rings is slightly different in the two molecules [63.22 (13) and 61.81 (14)°].

“…The reactivity of these sesquiterpenes and its derivatives has been studied extensively by our team in order to prepare new products having biological proprieties (Lassaba et al, 1998;Chekroun et al, 2000;El Jamili et al, 2002;Sbai et al, 2002;Dakir et al, 2004). Indeed, these compounds were tested, using the food poisoning technique, for their potential antifungal activity against the phytopathogen Botrytis cinerea (Daoubi et al, 2004).…”

Section: S1 Commentmentioning

confidence: 99%

1-Isopropyl-4,7-dimethyl-2,8-dinitronaphthalene

Chakkar¹,

Oughris²,

Benharref³

et al. 2012