473-54-1

Usage

Uses

trans-2-Pinanol is an essential oil component found in a variety of plants.

InChI:InChI=1/C10H18O/c1-9(2)7-4-5-10(3,11)8(9)6-7/h7-8,11H,4-6H2,1-3H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 473-55-2 2,6,6-trimethylbicyclo[3.1.1]heptane 
• 80-15-9 Cumene hydroperoxide 
• 766-07-4 cyclohexyl hydroperoxide 
• 4952-03-8 1-methylcyclohexane hydroperoxide 
• 5813-49-0 nitrosyl acetate 
• 13293-47-5 2αH-pinan-3α-ylamine 
• 80-56-8 Pinene 
• 473-72-3 pinonic acid 
• 28664-03-1 (3-ethoxycarbonyl-2,2-dimethyl-cyclobutyl)-acetic acid ethyl ester 
• 28664-02-0 pinic acid 
• 5405-84-5 pinan-2-yl hydroperoxide 
• 24903-95-5 nopinone 
• 917-54-4 methyllithium 

Downstream Products

• 2451-01-6 cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate 
• 586-62-9 Terpinolene 
• 25580-62-5 1,8-dichloro-trans-p-menthane 
• 4497-96-5 1-Chloro-4-(1-chloro-1-methyl-ethyl)-1-methyl-cyclohexane 
• 98-55-5 terpineol 

Relevant academic research and scientific papers

POLYMERIC MATERIALS

The present invention relates to a polymer comprising as part of its polymer backbone a moiety of Formula (II): where one of R6 to R10 represents A-O— and one of R6 to R10 represents —O—B and the remainder of R6 to R10 represent H, where A and B represent the remainder of the polymer backbone and may be the same or different.

Studies on the Oxidation of cis- and trans-Pinane with Molecular Oxygen

The pinanes are preferably attacked at the tertiary C-H bond in 2-position, but products of the oxidative attack at the secondary C-H-bonds in 3- and 4-position are also found.At 100 deg C cis-pinane is attacked more easily than trans-pinane (kcis : ktrans = 6.4), the relative rates of attack at the secondary C-H bonds in positions 3 and 4 with respect to the tertiary C-H bond in 2-position were also determined (in cis-pinane ksec : ktert = 0.027; in trans-pinane ksec : ktert = 0.20).After the attack at the 2-C-H bond the radical formed can either react with oxygen to form the corresponding cis- and trans-peroxy radicals and further to give cis- and trans-2-hydroperoxy pinane or fragmentate to the monocyclic radical derived from α-terpinene, giving as a final products α-terpinene hydroperoxide and the bicyclic 8-hydroperoxy 4,4,8-trimethyl 2,3-dioxabicyclononane.The corresponding alcohols were found after reduction with sodium sulphite.The oxidation at position 2 of the pinanes delivers not only the cis- and trans-hydroperoxide but also, as short-lived intermediates, the corresponding 2-pinanyloxy radicals.These radicals fragmentate forming a carbon radical with cyclobutane structure whose oxidation products were identified.Besides fragmentation of the 2-pinanyloxy radical also an intramolecular H-transfer from the methyl group in 9-position to the oxygen of the trans-pinanyloxy radical takes place leading to 9-hydroperoxy trans-pinane-2-ol.

Studies on the Decomposition of Alkyl Hydroperoxides by Different Catalysts

The catalytic decomposition of cumene, 1-methylcyclohexyl and cyclohexyl hydroperoxides was studied in cyclohexane, cis- and trans-1,4-dimethylcyclohexane and cis-pinane as the solvents.The stearates and the acetylacetonates of manganese, cobalt and chromium, the acetylacetonates of molybdenum and vanadium, n-butyl orthoborate and n-butyl metaborate were used as the catalysts.The chromium-, vanadium-, molybdenum- and boron-containing catalysts brought about some Hock-type decomposition of cumene hydroperoxide and thus proved to be acidic.Of these more of less acidic catalysts only molybdenyl acetylacetonate effected a partially stereospecific hydroxylation of the tertiary C-H-bonds in cis- and trans-1,4-dimethylcyclohexane.The well-known selectivity of chromium catalysts for the ketone formation during the decomposition of secondary hydroperoxides is caused by the catalytic oxidation of secondary alcohols by hydroperoxides in the presence of chromium compounds.In the presence of all the catalysts used the free-radical pathways of the hydroperoxide decomposition predominated, and the attack of the intermediate radicals on the starting hydroperoxide was more important than the attack on the solvent molecules.

Rearrangement of Pinane Derivatives. Part 8. Deamination of 2αH-Pinan-3α-ylamine

Solvolysis of 2αH-pinan-3α-yl toluene-p-sulphonate has been shown to proceed with concomitant 1,2-hydride shift to give the pinan-2-yl carbocation.Contrary to earlier reports, this species reacts normally to give, in good yield, pinan-2-yl substitution products.In contrast the pinan-3-ylamines react via a similar route, but give much smaller amounts of pinan-2-yl products.The usual reasons for differences between solvolysis and deamination (i.e. the intermediacy of diazonium ions and/or high-energy ions) can be discounted, and possible reasons for the differences in behaviour are discussed.