20731-23-1Relevant articles and documents
-
Crandall,J.K. et al.
, p. 1428 - 1433 (1971)
-
Preparation of ω-hydroxynonanoic acid and its ester derivatives
Kula, Jozef,Smigielski, Krzysztof,Quang, Thuat B.,Grzelak, Iwona,Sikora, Magdalena
, p. 811 - 817 (1999)
Methyl ricinoleate was ozonized in methanol or in acetic acid and the intermediate hydroperoxides were reduced electrochemically on Pb-cathode to give 9-hydroxynonanoic acid 1 in high yields. The acid 1 was also prepared by direct castor oil ozonolysis in methanol followed by sodium borohydride reduction of the intermediate hydroperoxides. The cost of the electricity for the electroreduction was at least 30 times lower as compared with sodium borohydride consumption. 9-Hydroxynonanoic acid was then transformed to alkyl 9-acetoxynonanoates 3a-3d, for which 1H nuclear magnetic reasonance, mass, and infrared spectra are given. Esterification of the hydroxy acid 1 with boric acid and pyrolysis of the resultant orthoborates produced 8-nonenoic acid 4 in a 45% yield. Reaction of 4 with lower aliphatic alcohols in presence of Amberlyst 15 produced alkyl 8-noneates 5a-5d along with some amounts of a cis/trans mixture of alkyl 7-noneates.
SYNTHESIS OF PHEROMONES AND RELATED MATERIALS VIA OLEFIN METATHESIS
-
Paragraph 0110; 0230, (2018/09/12)
Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.
Z -selective ethenolysis with a ruthenium metathesis catalyst: Experiment and theory
Miyazaki, Hiroshi,Herbert, Myles B.,Liu, Peng,Dong, Xiaofei,Xu, Xiufang,Keitz, Benjamin K.,Ung, Thay,Mkrtumyan, Garik,Houk,Grubbs, Robert H.
supporting information, p. 5848 - 5858 (2013/05/22)
The Z-selective ethenolysis activity of chelated ruthenium metathesis catalysts was investigated with experiment and theory. A five-membered chelated catalyst that was successfully employed in Z-selective cross metathesis reactions has now been found to be highly active for Z-selective ethenolysis at low ethylene pressures, while tolerating a wide variety of functional groups. This phenomenon also affects its activity in cross metathesis reactions and prohibits crossover reactions of internal olefins via trisubstituted ruthenacyclobutane intermediates. In contrast, a related catalyst containing a six-membered chelated architecture is not active for ethenolysis and seems to react through different pathways more reminiscent of previous generations of ruthenium catalysts. Computational investigations of the effects of substitution on relevant transition states and ruthenacyclobutane intermediates revealed that the differences of activities are attributed to the steric repulsions of the anionic ligand with the chelating groups.
