20434-86-0Relevant articles and documents
Studies of nitrile oxide cycloadditions, and the phenolic oxidative coupling of vanillin aldoxime by Geobacillus sp. DDS012 from Italian rye grass silage
Kelly, David R.,Baker, Simon C.,King, David S.,De Silva, Deepa S.,Lord, Gwyn,Taylor, Jason P.
, p. XX787-796 (2008/09/17)
During studies directed towards the discovery of nitrile hydrolysing enzymes from thermophiles, vanillin aldoxime was incubated with the thermophilic organism, Geobacillus sp. DDS012 isolated from Italian rye grass (Lolium multiflorum) silage. The predominant product was a dihydro-dimer, which could only be characterised by LC-MS. This was initially imagined to be the product of cycloaddition of vanillin aldoxime with the corresponding nitrile oxide, but preparation of the supposed adduct and model studies excluded this possibility. The rate constant for the second order dimerisation of 4-O-acetyl vanillin nitrile oxide was measured (1.21 × 10-4 M-1 s -1, 0.413 M, 25 °C) and the 13C-NMR signal for the nitrile oxide carbon was observed (δC 34.4, br. t 1J13C,14N circa 50 Hz). Treatment of vanillin aldoxime with potassium persulfate and iron sulfate gave material with the same LC-MS properties as the natural product, which is therefore identified as 5,5′-dehydro-di-(vanillin aldoxime) 1d formed by phenolic oxidative coupling. This journal is The Royal Society of Chemistry.
SYNTHESIS OF ISOXAZOLES BEARING METHOXYCARBONYL AND FORMYL GROUPS BY 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDES TO OLEFINIC AND ACETYLENIC DIPOLAROPHILES
Farina, Francisco,Fraile, M. Teresa,Martin, M. Rosario,Martin, M. Victoria,Guerenu, Ana Martinez de
, p. 285 - 292 (2007/10/02)
The 1,3-dipolar cycloaddition of benzo-, bromoformo- and acetonitrile oxides to enamino ester (1) and acetylenic esters (2,3) afforded functionalized isoxazoles in moderate to good yields.Cycloadditions with the enamino ester (1) gave the corresponding me
ADDITION OF PICOLINES TO BENZONITRILE OXIDE. A DIVERGING PATH WITH 4-PICOLINE
Albini, Franca Marinone,Franco, Rita De,Bandiera, Tiziano,Gruenager, Paolo,Caramella, Pierluigi
, p. 1 - 7 (2007/10/02)
Biscycloadducts are formed by exposing 2- and 3-picoline to benzonitrile oxide. 4-picoline instead affords products of condensation on the methyl group.