19427-85-1Relevant academic research and scientific papers
Oxidation of terpenoid diols with chlorine dioxide. Easy preparation of α-hydroxyketones
Frolova,Popov,Bezuglaya,Alekseev,Slepukhin,Kuchin
, (2014)
Oxidative dehydrogenation of vicinal diols of bornane and pinane type with chlorine dioxide in dimethylformamide has yielded α-hydroxyketones with high selectivity. 3α-Hydroxy-10β-pinane-4-one has been prepared for the first time with yield of 63-65%; the
Oxazoline N-oxide mediated [2 + 3] cycloadditions. Application to a formal synthesis of (+)-carpetimycin A.
Mauduit,Kouklovsky,Langlois,Riche
, p. 1053 - 1056 (2007/10/03)
[formula: see text] Cycloaddition between gamma,delta-unsaturated beta-enamino ester 9 and camphor-derived oxazoline N-oxide 8 afforded a single adduct, 14. Dipolarophile 9 proved to be very reactive despite the substitution on the double bond. Stereoselective sodium cyanoborohydride reduction of the imminium intermediate 14a gave rise stereoselectively to beta-amino ester derivative 15a. Oxidative acidic hydrolysis, oxidation of the resulting aldehyde 18, deprotection, and cyclization afforded the beta-lactam 23, a direct precursor of (+)-carpetimycin A.
Minor Products in Photoreactions of α-Diketones with Arenes. Abstraction of Hydroxylic Hydrogen by Triplet Carbonyl
Rubin, Mordecai B.,Gutman, Arie L.
, p. 2511 - 2515 (2007/10/02)
Photochemical reactions of cyclic saturated α-diketones in toluene or p-xylene produce 1:1 adducts as major products and smaller amounts of reduced diketone and bibenzyls, as expected from previous work.In addition, reaction of BOD gave 2percent of the decarbonylation product, p-methylbenzyl cyclohexyl ketone; reaction of camphorquinone gave a mixture of decarbonylation products (10percent total) including saturated and unsaturated monoketones.These compounds were secondary products arising from reaction of photoexcited diketone with the initially formed adducts; quenching andsensitization studies showed that triplet states of α-diketones were involved in both primary and secondary reactions.The decarbonylation products were also formed by reaction of benzophenone triplets or of tert-butoxy radicals with adducts.Deuterium labeling of the adducts was employed to demonstrate that the decarbonylation process involves abstraction of hydroxylic hydrogen.
