Vandewiele, Nick M., et al. Journal of Analytical and Applied Pyrolysis 90.2 (2011): 187-196.
From Scheme 1 (cis-2-pinanol) and Scheme 2 (trans-pinanol), it can be seen that the stepwise mechanism starts with the opening of the cyclobutane ring of the 2-pinanol reactant (1) via carbon-carbon bond cleavage, leading to cyclic hexanol radicals with methyl and isopropenyl substituents at the 1,4- (compound 2) and 1,2-positions (compound 3). The remaining two C-C bond cleavage possibilities of the cyclobutane ring were not considered, as they would generate unstable diradicals containing primary carbon radicals. Furthermore, through quantum chemical calculations, due to the boat or twisted conformations of the cyclohexane ring, the transition-state structures of these remaining ring-opening reactions in the thermal rearrangement of cis- and trans-pinanes are unfavorable in energy, whereas the chair conformer of the cyclohexane ring is opposite in the ring-opening reaction transition-state structures leading to diradicals with tertiary radical carbon atoms. At 793 K, the bond dissociation energies (BDEs) of the primary carbon diradicals are 15 kJ mol-1 higher than those leading to the C-C cleavage diradicals 2 and 3. Subsequently, the cleavage of the weakened carbon-carbon bonds at the two radical carbon centers of the diradicals 3 and 2 leads to the acyclic substituted 1,6-octadiene-4-ol and isocampholide. An alternative reaction pathway of diradical intermediate 2 leads to the monocyclic p-menthane-type compound 5, terpineol, via a [1,5]-hydrogen shift. The acyclic primary thermal decomposition products, camphor and isocamphor, are reported to undergo further cyclic olefination through a six-membered transition state, forming cyclopentanol derivatives plinol and compound 8. However, the cyclopentanol derivative 8 was not detected in the experimental reactor effluent. Owing to the relative positions of the hydroxyl and isopropenyl groups in compound 8, the latter can be rearranged back into an acyclic enone-type compound 9 via a retro-ene reaction, where the γ-hydrogen atom is transferred to the unsaturated center through a six-electron cyclic transition state. The possibility of the analytical setup not being able to detect compound 8 was ruled out, as the parallel isomerization pathway forming the polyhydroxybenzene isomers (7) was detected by this setup. Therefore, it is concluded that the rate of formation of 9 from 8 is significantly higher than the cyclic olefination G, and 8 is considered to be a fast-reacting intermediate.
What is the product name of the chemical compound with CAS number 4948-28-1?
The product name is Cis-2-Pinanol.
What are some synonyms for Cis-2-Pinanol?
Some synonyms for Cis-2-Pinanol are Alpha-Pinanol and Bicyclo[3.1.1]heptan-2-ol.
What is the IUPAC name of Cis-2-Pinanol?
The IUPAC name of Cis-2-Pinanol is (1R,2S,5R)-2,7,7-trimethylbicyclo[3.1.1]heptan-2-ol.
What is the molecular weight of Cis-2-Pinanol?
The molecular weight of Cis-2-Pinanol is 154.25 g/mol.
What is the boiling point of Cis-2-Pinanol?
The boiling point of Cis-2-Pinanol is 203.1ºC at 760 mmHg.
What is the melting point of Cis-2-Pinanol?
The melting point of Cis-2-Pinanol is 68-71ºC.
What is the flash point of Cis-2-Pinanol?
The flash point of Cis-2-Pinanol is 80.8ºC.
What is the purity of Cis-2-Pinanol?
The purity of Cis-2-Pinanol is 96%.
What is the density of Cis-2-Pinanol?
The density of Cis-2-Pinanol is 0.969 g/cm³.
What are some typical applications of Cis-2-Pinanol?
Cis-2-Pinanol is typically used as a perfume.
CONNECT WITH US
Interested in our Services & Products ?
Need detailed information?
Terms & Conditions
Privacy Policy | Cookie Policy | Copyright © 2024 Alfa Chemistry. All rights reserved.
PAGE TOP
