Reaction mechanism of direct episulfidation of caryophyllene and humulene.

Abstract

Direct episulfidations of caryophyllene or humulene with elemental sulfur were examined by means of gas chromatography. Caryophyllene-6,7-episulfide was formed at an early stage in a reaction of the caryophyllene and elemental sulfur at 120 degrees C. Caryophyllene-3,6-sulfide and polymer compounds were formed after the episulfidation. Formations of the these compounds were related to the disappearance of the caryophyllene-6,7-episulfide. Isomerization from the caryophyllene to isocaryophyllene was also observed during the reaction. In the reaction of humulene with elemental sulfur, humulene-6,7-episulfide was initially produced and then converted to humulene-9,10-episulfide. It was assumed that the polymer compound in the reaction of humulene with sulfur was related to the disappearance of the both humulene episulfides.

DOI: 10.1080/14786410701591903

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@article{Ashitani2008ReactionMO, title={Reaction mechanism of direct episulfidation of caryophyllene and humulene.}, author={T. Ashitani and Anna-Karin Borg-Karlson and Koki Fujita and Shizuo Nagahama}, journal={Natural product research}, year={2008}, volume={22 6}, pages={495-8} }