Oxygen-containing bicyclic monoterpenes.¹H,¹³C and¹⁷O NMR Spectroscopic and X-ray diffraction studies of seven oxidation products of (+)-3-carene

Technical Note: Preparation and purificationof atmospherically relevant α-hydroxynitrate esters of monoterpenes

“…Purification of the crude oil by column chromatography (12 g SiO2, 0-40% EtOAc/Hex) yielded cis-4-caranone as a clear, colorless oil (53% yield) Rf 0.51 (5% EtOAc:Hex; anisaldehyde); 1 H NMR (400 MHz, Chloroform-d) δ 2.54 (ddd, J = 18.0, 8.4, 1.0 Hz, 1H), 2.44 -2.25 (m, 3H), 1.33 -1.20 (m, 1H), 1.14 -0.99 (m, 5H), 0.97 (d, J = 6.4 Hz, 3H), 0.86 (s, 3H); 13 C NMR (101 MHz, Chloroform-d) δ 216.79, 41.99, 36.84, 29.77, 27.91, 22.83, 20.34, 19.47, 14.89, 14.11 ppm. Spectral data is consistent with literature reports (Kolehmainen et al, 1993). 15…”

Technical note: Preparation and purification of atmospherically relevant <i>α</i>-hydroxynitrate esters of monoterpenes

“…The facile rearrangements of α-pinene with both Brønsted and Lewis acids (Kaminska et al, 1992) can be thought to proceed via a nonclassical isobornyl cation (18) (Kong et al, 2010). We expected the reaction with bismuth nitrate to generate a complex mixture of products due to the many reactive sites.…”

Biotransformation of (1S)-2-Carene and (1S)-3-Carene by Picea abies Suspension Culture

“…The biotransformation products were identified by gas chromatography - mass spectrometry by the use of the MS library Wiley 275 and NIST or by comparisons of their retention times and mass spectra with those of the synthesized reference substances [ 24 , 25 , 26 , 27 , 28 ,29,30]. The relative quantitative yield of each product (in %) was determined as the GC-MS integration area of that product divided by the GC-MS integration area of all products.…”

“…(1S)-3-Caren-2-one ( 9 ) [ 23 , 27 , 28 ]. The method was identical to that described for the preparation of (1 S )-2-caren-4-one.…”