2004
DOI: 10.1021/ol036298q
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4-Isocyano-2,2,6,6-tetramethylpiperidin- 1-oxyl:  A Valuable Precursor for the Synthesis of New Nitroxides

Abstract: To enrich the limited set of isonitriles typically employed, 4-isocyano-2,2,6,6-teramethylpiperidin-1-oxyl (1) is proposed as an isonitrile bearing a nitroxyl moiety. Isocyanide 1 was used in some reactions characteristic of isonitriles. Isoselenocyanate, amides (products of Passerini and Ugi reactions), and tetrazole derivative were obtained. The EPR spectra of the urea derivative 5b and a product of an Ugi reaction 7 (both dinitroxides) were analyzed. [structure: see text]

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Cited by 19 publications
(17 citation statements)
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“…The dehydration of 2 with gaseous phosgene [38] or diphosgene leads to 4-isocyano-2,2,6,6-tetramethylpiperidine-1-oxyl (3), which was selenated with metallic selenium to give 4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl (4) [39].…”
Section: Resultsmentioning
confidence: 99%
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“…The dehydration of 2 with gaseous phosgene [38] or diphosgene leads to 4-isocyano-2,2,6,6-tetramethylpiperidine-1-oxyl (3), which was selenated with metallic selenium to give 4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl (4) [39].…”
Section: Resultsmentioning
confidence: 99%
“…The reagent is able to selenate amides and formamides by substitution of the oxygen atom [40,41]. The condensation of dichlorphenylphosphine (7) with magnesium in THF [42][43][44][45][46] yields pentaphenylpentaphospholane [(PhP) 5 , (8)] SCHEME 1 (i) HCOOEt [38] (ii) COCl 2 [38] or ClCOOCCl 3 (diphosgene) (iii) Se, CHCl 3 [39] (iv) (5a-h) HX, benzene (6a,b) HX/NaX. (62% yield).…”
Section: Resultsmentioning
confidence: 99%
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“…However, some urea nitroxides have already been reported Part III: [1]. [11][12][13][14][15][16][17]. Here, in relation to our previous studies on the nitroxides containing sulfur functional groups [1], we present the synthesis, mass spectral features, and some pesticidal properties of the novel (thio)ureas bearing the nitroxyl moiety [18].…”
Section: Introductionmentioning
confidence: 92%