7754-22-5

Usage

Uses

There is no information provided in the materials about the specific applications or uses of 2,2,4,4-Tetramethyl-3-pentanone oxime. However, based on the analysis using EPR spectroscopy, it can be inferred that TPO may have potential applications in the field of materials science, particularly in the study of irradiated materials and their properties.

InChI:InChI=1/C9H19NO/c1-8(2,3)7(10-11)9(4,5)6/h11H,1-6H3

Upstream product

• 33802-06-1 di-tert-butyliminoxyl 
• 20696-89-3 cyclohexene-d₂^1,2 
• 110-83-8 cyclohexene 

Downstream Products

• 105456-89-1 2,6-Di-tert-butyl-4-(1-tert-butyl-2,2-dimethyl-propylideneaminooxy)-4-methyl-cyclohexa-2,5-dienone 

Relevant academic research and scientific papers

Mechanisms of reaction of aminoxyl (nitroxide), iminoxyl, and imidoxyl radicals with alkenes and evidence that in the presence of lead tetraacetate, N-hydroxyphthalimide reacts with alkenes by both radical and nonradical mechanisms

1,2-Dideuterio-cyclohexene, 1,2-dideuterio-cyclooctene, and trans-3,4-dideuterio-hex-3-ene were reacted with three >NO. radicals: 4-hydroxyTempo, di-tert-butyliminoxyl, both used as the actual radicals, and phthalimide-N-oxyl (PINO) generated from N-hydroxyphthalimide (NHPI) by its reaction with tert-alkoxyl radicals (t-RO.) and with lead tetraacetate. In all cases, except the NHPI/Pb(OAc)4 system, only mono >NO.-substituted alkenes were produced. The 2H NMR spectra imply that 88-92% of monoadducts were formed by the initial abstraction of an allylic H-atom, followed by capture of the allylic radical by a second >NO., while the remaining 12-8% appear to be formed by an initial addition of >NO. to the double bond followed by H-atom abstraction by a second >NO.. A substantial and sometimes the major product formed with the NHPI/Pb(OAc)4 system has two PINO moieties added across the double bond. Since such diadducts are not formed with the NHPI/t-RO. system, a heterolytic mechanism is proposed, analogous to that known for the Pb(OAc)4-induced acetoxylation of alkenes. A detailed analysis of the NHPI/Pb(OAc) 4/alkene products indicates that monosubstitution occurs by both homolytic and heterolytic processes.

Limitations on the Persistence of Iminoxyls: Isolation of tert-Butyl 1,1-Diethylpropyl Ketiminoxyl and Related Radicals

A series of iminoxyl radicals of the general formula R(C=NO?)R1, with R and R1 usually tertiary, was synthesized in a search for radicals of increased persistence. Three new radicals were isolated as blue liquids: Et3C(C=NO?)Bu-t (1), t-C5H11(C=NO?)Bu-t (2), and (t-C5H11)2C=NO? (3). Oxidation of oximes Et3C(C=NOH)Ph (4H), PhCH2CMe2(C=NOH)Bu-t (5H), PhCMe2(C=NOH)Bu-t (6H), and Me2CH(C=NOH)C5H11-t (7H), among others, did not lead to isolable iminoxyls. A new, convenient synthesis of symmetrical tertiary imines from tert-RCl, tert-RCN, and Na is described. Radical t-Bu2C=NO? (8) and cyclohexene readily gave the allylic substitution product, 2,2,4,4-tetramethyl- 3-hexanone O-(2′-cyclohexen-1′-yl)oxime.