51131-99-8

Upstream product

• 7785-70-8 (+)-α-pinene 
• 807306-71-4 3,7-bis(dimethylamine)phenothiazonium 
• 67-63-0 isopropyl alcohol 
• 80-56-8 Pinene 
• 80-56-8 rac-α-pinene 

Downstream Products

• 1674-08-4 (-)-trans-pinocarveol 
• 16812-40-1 pinocarvone 
• 547-61-5 pinocarveol 
• 58434-29-0 myrtenyl hydroperoxide 
• 515-00-4 myrtenol 
• 564-94-3 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde 

Relevant academic research and scientific papers

IBX as a catalyst for dehydration of hydroperoxides: Green entry to α,β-unsaturated ketones: Via oxygenative allylic transposition

A catalytic transformation of allylic hydroperoxides into α,β-unsaturated carbonyl compounds using IBX as a dehydration catalyst is described. The combination of a singlet oxygen ene reaction and the IBX-catalyzed dehydration provides α,β-unsaturated carbonyl compounds from alkenes via oxygenative allylic transposition with H2O as the only byproduct.

IRA-200 resin-supported platinum(II) complex for photooxidation of olefins

Cyclometalated platinum(II) 4,6-diphenyl-2,2′-bipyridine complex is supported on a commercially available cationic ion-exchange resin (amberlite IRA-200). Photophysical and ESR determinations indicate that the combined photosensitized system is able to generate singlet oxygen with high quantum yield upon irradiation of light in the visible region. The platinum(II) complex loaded on IRA-200 resin is stable and the photooxidation occurs in an environmentally friendly way. Only a simple filtration is needed to recycle the expensive metal catalyst.

Ring-opening metathesis polymer sphere-supported seco-porphyrazines: Efficient and recyclable photooxygenation catalysts

Crossover Linstead macrocyclization of norbornenyl-tagged diaminomaleonitrile with dipropylmaleonitrile gave the corresponding magnesium diaminohexapropylporphyrazine, which was subsequently converted into its zinc seco-derivative. Polymerization gave the corresponding ROMPgel and ROMPsphere (ROMP = ring-opening metathesis polymer) reagents, the latter of which proved efficient as an immobilized catalyst for the sensitized production of singlet oxygen for the purification-minimized parallel synthesis of endoperoxides and ene adducts.

A family of new 1,2,4-trioxanes by photooxygenation of allylic alcohols in sensitizer-doped polymers and secondary reactions

Type II photooxygenation (singlet oxygen) is described as a synthetically useful way for the preparation of allylic hydroperoxides and endoperoxides using sensitizer-adsorbed or covalently sensitizer-doped polymeric (macro- or nanosized) containers. Facil

Photooxygenation in polystyrene beads with covalently and non-covalently bound tetraarylporphyrin sensitizers

Two reaction protocols are described which involve the use of polymer supports as reaction media for photooxygenation processes: 1) The use of polystyrene beads (PS) loaded with tetraphenyl- (TPP) or tetratolylporphyrin (TTP), swollen with the substrate in an appropriate organic solvent and subsequent irradiation under air. Products were isolated simply by dissolution in alcoholic solvents and filtration. 2) Covalently linked tetrastyrylporphyrin in polystyrene-divinylbenzene beads were synthesized by emulsifier-free emulsion polymerization and directly used for the photooxygenation protocol described above. The latter alternative allows also the use of less polar solvents for the extraction of the oxygenation products from the polymer beads. From the sensitizer loading degree, an optimal substrate/sensitizer molar ratio of 1,000-2,000 was determined and recyclization is possible for at least five times resulting in a minimum turnover number (with respect to the sensitizer TTP) of 5 × 104 (after five cycles). Both approaches were applied to the ene reaction of singlet oxygen with citronellol (1), the regioisomeric pinenes 3 and 5, and the allylic alcohols 9a - c, respectively, as well as to the [4 + 2]-cycloadditions of singlet oxygen to sorbinol (7) and the chiral diene 11.

Sustainable photochemistry: Solvent-free singlet oxygen-photooxygenation of organic substrates embedded in porphyrin-loaded polystyrene beads

A solvent-free photooxygenation process that uses organic substrates embedded in porphyrin-loaded polystyrene beads as solid support is described and applied for ene- and [4+2]-cycloaddition reactions involving singlet oxygen (1Δg).

Azidohydroperoxidation of pinenes: Stereoselectivity pattern and the first X-ray structure of a 2-azidohydroperoxide

The photoinduced electron transfer of azide anions in the presence of an excited organic dyestuff, oxygen, and α- or β-pinene, respectively, gave 2-azidohydroperoxides in excellent regio- and good diastereoselectivity.

Peroxides as plant constituents. 6. Hydroperoxides from the blossoms of Roman camomile, Anthemis nobilis L

From the ethanol extract of the blossoms of Anthemis nobilis L. (syn. Chamaemelum nobile L.), six new hydroperoxides (1-6) were isolated, besides the known 1 beta-hydroperoxyisonobilin (7). The structures were elucidated by spectroscopic methods and in some cases ascertained by synthesis. Compounds 2 and 3 show a medium antibacterial activity.

INTERVENTION D'UN MECANISME IONIQUE DANS LA PHOTOOXYGENATION SENSIBILISEE DE L'α-PINENE EN MILIEU PROTIQUE

In protic media, the (singlet oxygen)-(α-pinene) ene reaction is partially deviated towards the formation of bifunctional products (5, 7a, 7b) which provides evidence for zwitterionic intermediates.