4176-04-9Relevant academic research and scientific papers
Molecular rearrangements of α-(trans)- and β-(cis)-3,4-epoxycaranes in acid media
Polovinka,Korchagina,Gatilov,Vyglazov,Zenkovets,Barkhash
, p. 1283 - 1291 (2007/10/03)
Configuration of the oxirane ring in stereoisomeric 3,4-epoxycaranes affects the direction of their skeletal rearrangements in liquid (HSO3F-SO2FCl) and over solid (TiO2/SO42-) superacids; in the latter case, compounds postulated as intermediates in the liquid-phase process have been isolated.
Catalytic transformations of 3-carene oxide over alumina-rare earth oxide catalysts
Jayasree, J.,Narayanan, C. S.
, p. 577 - 580 (2007/10/02)
Isomerization of 3-carene oxide over binary oxide catalysts like Al2O3-Y2O3, Al2O3-Sm2O3, Al2O3-Eu2O3, Al2O3-Pr6O11 and Al2O3-Nd2O3 at 80 deg C and 110 deg C has been studied. 3,6,6-Trimethylbicyclohexane-3-carboxaldehyde and caranone are the major products formed at 80 deg C.Rise in reaction temperature results in an increase in epoxide transformation and an irregular variation in the yield of products.
Synthesis of Some Conjugated Caradienes from 3-Carene by the Wittig Reaction and Their Reactivity in the Diels-Alder Reaction
Lajunen, Marja
, p. 13181 - 13198 (2007/10/02)
The applicability of the Wittig reaction for the preparation of conjugated cis-caradienes was studied by the preparation of 4-methyl-3(10)-carene (27).The method was applied for the study of the synthesis of 3-vinyl-3-apocarene (6), 4-methylene-3(10)-carene (7), 4-methyl-2-methylene-3(10)-carene (8), 4-isopropenyl-3-carene (9) and 4-isopropenyl-3-caren-2a-ol (11) starting from 3-carene (20).The reactivity of conjugated cis-caradienes 6,7 and 9 in the Diels-Alder reaction has also been studied.
Oxygen-containing Bicyclic Monoterpenes. 1H, 13C and 17O NMR Spectroscopic and X-Ray Diffraction Studies of Seven Oxidation Products of (+)-3-Carene
Kolehmainen, Erkki,Laihia, Katri,Heinaenen, Mika,Rissanen, Kari,Froehlich, Roland,et al.
, p. 641 - 648 (2007/10/02)
Seven oxidation products of (1S,6R)-(+)-3,7,7-trimethylbicyclohept-3-ene 1; (1S,6R)-3,7,7-trimethylbicyclohept-3-en-2-one (3-caren-2-one) 2, (1S,6R)-3,7,7-trimethylbicyclohept-3-en-5-one (3-caren-5-one) 3, (1S,6R)-3,7,7-trimethylbicyclohept-3-ene-2,5-dione (3-carene-2,5-dione) 4, (1S,3S,4R,6R)-(+)-3,7,7-trimethylbicycloheptene 3,4-trans-oxide (trans-3,4-epoxy-3-carene) 5, (1S,3R,4R,6R)-3,7,7-trimethylbicycloheptane-3-exo-4-endo-diol (carane-3-exo-4-endo-diol) 6 and (1S,2R,4R,5R)-1-methyl-4-exo-(1-hydroxy-1-methylethyl)bicyclohexan-2-endo-ol 7 and (1S,6R)-3-endo-7,7-trimethylbicycloheptan-4-one (trans-4-caranone) 8 have been obtained by oxidation with tert-butylchromate, selenium dioxide, hydrogen peroxide and peracetic acid.The 1H, 13C and 17O NMR spectra of the purified oxidation products have been recorded and assigned.In addition to C,H-COSY spectra, the 1J(C,H) coupling constants were especially useful in 13C NMR spectral assignment.The differentiation between isomeric ketones 2 and 3 is based on a clear difference in the 13C NMR shifts of the double bond methyl.The stereochemical structure elucidation of oxide 5 is based on lanthanide shift reagent induced effects.For ketone 8, molecular mechanics (MM) calculations and comparison of experimental and theoretical 3J(H,H) coupling constants are needed for a final structure elucidation.The assignment of 17O NMR lines of diols 6 and 7 is based on literature values.The crystal structures and absolute configurations of pure enantiomers of diols 6 and 7 have been determined by X-ray diffraction.Crystal data: a = 7.659(2), b = 10.804(3), c = 25.509(4) Angstroem, orthorhombic, space group C2221, Z = 8 (6) and a = 8.076(4), b = 8.836(2), c = 12.487(3) Angstroem, orthorhombic, space group P212121, Z = 4 (7).
Transformations of 3-carene oxide at rhenium-containing catalysts
Manukov, E. N.,Bazhina, G. N.
, p. 106 - 110 (2007/10/02)
The transformations of 3-carene oxide at rhenium-containing catalysts were studied.The introduction of rhenium into the catalytic system significantly increases the reaction rate and leads to the formation of compounds not previously encountered in the products from the isomerization of 3-carene oxide, i.e., 3-carene, 3(10),4-caradiene, 3,3,6-trimethylcycloheptanone, and 3-caren-10-ol.
LIGHT-MEDIATED TRANSFORMATIONS OF OLEFINS INTO ALCOHOLS: REACTIONS OF HYDROXYL RADICALS WITH CYCLOALKENES
Sonawane, H. R.,Nanjundiah, B. S.,Kelkar, R. G.
, p. 6673 - 6682 (2007/10/02)
Reactions of hydroxyl radicals, generated by photodecomposition of hydrogen peroxide in acetonitrile, with a wide variety of cycloalkenes have been examined.The results show that the major reaction is the addition of hydroxyl radicals to the less substituted end of the double bond, furnishing the secondary alcohols.The reactivity pattern and the observed regio- and stereoselectivity clearly reveal that the steric parameters associated with the substrates play a dominant role in directing the addition reactions.More importantly, this study led to the development of a new methodology for the facile conversions of olefins essentially into secondary alcohols, and includes a few examples which demonstrate the potential of the method.
STEREOCHEMICAL CONTROL ON THE PHOTOCHEMISTRY OF α-METHOXY-β,γ-CYCLOPROPYL CYCLIC KETONES : REACTIONS OF EPIMERIC 3-METHOXY-4-CARANONES
Sonawene, H. R.,Nanjundiah, B. S.,Purohit, P. C.
, p. 3917 - 3918 (2007/10/02)
The two distinct photoreactions exhibited by epimeric ketones have been correlated with their stereochemistry.
