An alternative solvent-free synthesis of nopinone under ball-milling conditions: Investigation of reaction parameters.
A new method for the oxidative cleavage of β-pinene (1) yielding nopinone (2) with potassium permanganate as oxidant under solvent-free conditions was established. The reaction was performed in a conventional ball mill with use of a grinding auxiliary. The auxiliary has the ability to sorb liquid reactants such as 1 on its surface to make liquid(s) accessible for mechanical impact. Different reaction parameters and technical variables were assessed concerning their influence on yield and selectivity of 2. Different chemical parameters such as oxidants, grinding auxiliaries, and quantities were investigated. Also tuning parameters including milling time, rotation frequency, and number of milling balls were explored.
Szuppa
Tony
T
Institute for Technical Chemistry and Environmental Chemistry, Friedrich-Schiller University Jena, Lessingstraße 12, 07743 Jena, Germany.
Stolle
Achim
A
Ondruschka
Bernd
B
Hopfe
Wieland
W
D000081008:Bicyclic Monoterpenes; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D052918:Environmental Restoration and Remediation / Q000379:methods*; D055595:Mechanical Phenomena; D039821:Monoterpenes / Q000737:chemistry*; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D011196:Potassium Permanganate / Q000737:chemistry; D012399:Rotation; D012997:Solvents / Q000737:chemistry; D013997:Time Factors
D000081008:Bicyclic Monoterpenes; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D039821:Monoterpenes; D016877:Oxidants; D012997:Solvents; C476481:nopinone; D011196:Potassium Permanganate; C010789:beta-pinene