The Preparation and Stereochemistry of Pinane Derivatives

Banthorpe, D. V.; Whittaker, D.

doi:10.1021/cr60244a002

Cited by 65 publications

(30 citation statements)

References 77 publications

(132 reference statements)

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“…5 Hz splitting, is almost unique in having the same 6 value in CCI, and benzene solutions and is immediately assigned to H,. The almost zero value of A$$?…”

Section: R E S U L T S and Discussionmentioning

confidence: 92%

“…This is due to the width of the lines in this spectrum, which are all 0.5 Hz at half height, because of small, unresolved splittings.1° For example, both the 8 and 9 methyl peaks are ca. [1][2][3][4][5] Hz wide at half height. At this phenomenon is a general one in the pinane spectra it should be emphasised that the coupling constants obtained are significant only to this accuracy (f0.3 Hz).…”

Section: R E S U L T S and Discussionmentioning

confidence: 99%

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The NMR spectra and conformations of cyclic compounds–III: The conformations of some pinane derivatives

et al. 1969

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The 220 MHz 'H spectra of isoverbanone, nopinone and verbanone are reported. The spectra of the first two are completely assigned but that of verbanone only partially. The coupling constants obtained provide information about the conformation of these molecules. The isoverbanone molecule is almost Y shaped, but that of nopinone is between a Y shape anda half-chair conformation with the six membered ring bent away from the gem dimethyl groups. These conformations are consistent with the known steric interactions in these molecules.

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“…5 Hz splitting, is almost unique in having the same 6 value in CCI, and benzene solutions and is immediately assigned to H,. The almost zero value of A$$?…”

Section: R E S U L T S and Discussionmentioning

confidence: 92%

Section: R E S U L T S and Discussionmentioning

confidence: 99%

The NMR spectra and conformations of cyclic compounds–III: The conformations of some pinane derivatives

et al. 1969

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“…2-Pinanol can be synthesized from ␣-pinene and ␤-pinene [14] which are found in selected coniferous biomass [15] or in crude sulfate turpentine (CST) [16], a by-product of the paper industry. The catalytic hydrogenation of ␣-pinene yields mixtures of the diastereomers cis-pinane and trans-pinane with high stereoselectivity to the cis-hydrogenation product [17].…”

Section: Introductionmentioning

confidence: 99%

Kinetic study of the thermal rearrangement of cis- and trans-2-pinanol

Vandewiele

Reyniers

Marin

2011

Journal of Analytical and Applied Pyrolysis

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“…b-Pinene from turpentine sources is usually found in enantiopure (À) form (enantiomeric excess (ee) > 95 %). [7] The other enantiomer, (+)-b-pinene, prevails in citrus fruit oil. [8] A publication by Widmark and Blohm in 1957 reported the autoxidation rates of different monoterpenes (e.g., D…”

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confidence: 99%

Peculiarities of β‐Pinene Autoxidation

2011

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The thermal oxidation of the renewable olefin β-pinene with molecular oxygen was experimentally and computationally investigated. Peroxyl radicals abstract weakly bonded allylic hydrogen atoms from the substrate, yielding allylic hydroperoxides (i.e., myrtenyl and pinocarvyl hydroperoxide). In addition, peroxyl radicals add to the C=C bond of the substrate to form an epoxide. It was found that a relatively high peroxyl radical concentration, together with the high rate of peroxyl cross-reactions, make radical-radical reactions surprisingly important for this particular substrate. Approximately 60 % of these peroxyl cross-reactions lead to termination (radical destruction), keeping a radical chain length of approximately 4 at 10 % conversion. Numerical simulation of the reaction-based on the proposed reaction mechanism and known or predicted rate constants-demonstrate the importance of peroxyl cross-reactions for the formation of alkoxyl radicals, which are the precursor of alcohol and ketone products.

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The Preparation and Stereochemistry of Pinane Derivatives

Cited by 65 publications

References 77 publications

The NMR spectra and conformations of cyclic compounds–III: The conformations of some pinane derivatives

The NMR spectra and conformations of cyclic compounds–III: The conformations of some pinane derivatives

Kinetic study of the thermal rearrangement of cis- and trans-2-pinanol

Peculiarities of β‐Pinene Autoxidation

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