60269-12-7Relevant academic research and scientific papers
Acid-catalyzed isomerization of caryophyllene in the presence of SiO2 and Al2O3 impregnated with sulfuric acid
Romanenko,Tkachev
, p. 1051 - 1058 (2018/10/02)
The conversion of caryophyllene upon contact with Al2O3 and SiO2 impregnated with sulfuric acid was carried out, and the components of the resulting mixtures were identified. Having in hands such “standard” mixtures greatl
Solvolysis of caryophyllen-8β-yl derivatives: Biomimetic rearrangement- cyclization to 12-nor-8α-presilphiperfolan-9β-ol
Shankar, Sriram,Coates, Robert M.
, p. 9177 - 9182 (2007/10/03)
The solvolyses of caryophyllen-8β-yl p-nitrobenzoate (14-OpNB) and 15- norcaryophyllen-8β-yl tosylate (15-OTs) were investigated as potential model reactions for the biogenesis of the tricyclic presilphiperfolanol sesquiterpenes. Buffered solvolysis of 14-OpNB in 60% aqueous acetone at 125 °C afforded caryophyllene (3) as major product, accompanied by small amounts of caryophyllen-8β-ol (14-OH) and 5,8-cyclocaryophyllen-4α-ol (16). In contrast, 15-OTs underwent a stereospecific rearrangement-cyclization to 12- nor-8α-presilphiperfolan-9β-ol (17) upon solvolysis in 60% aqueous acetone at 75 °C. The structure and stereochemistry of this trans,cis,trans- tricyclo[6.2.1.05,11]-undecane derivative were established by NMR correlation spectroscopy and X-ray crystallography. Two different mechanisms (paths A and B) for the conversion of 15-OTs to 17 by initial 1,2-migration of either the external or internal cyclobutane ring bonds (C10 and C1) followed by π-σ cyclization onto the trans double bond are discussed.
