115262-05-0

Upstream product

• 6852-58-0 N-benzylidene tert-butylamine 
• 6852-58-0 (E)-N-benzylidene-2-methylpropan-2-amine 

Downstream Products

• 3378-72-1 N-tert-butylbenzylamine 
• 3532-55-6 2-benzylidene-N-(tert-butyl)acetoacetamide 
• 81375-57-7 3-acetyl-1-tert-butyl-4-phenyl-2-azetidinone 

Relevant academic research and scientific papers

Isomerization method for bis(amino-methyl)cyclohexane

An isomerization method for bis(amino-methyl)cyclohexane has an isomerization step for isomerizing bis(amino-methyl)cyclohexane in the presence of an imine compound represented by general formula (1) and one or more type of compound selected from the group comprising an alkali metal, an alkali-metal-containing compound, an alkali earth metal, and an alkali-earth-metal-containing compound. (In general formula (1), R1 and R2 each independently indicates a monovalent group selected from the group comprising a hydrogen atom, a substituted or un-substituted hydrocarbon group, a substituted or un-substituted alkoxy group, and an acyl group. (R1 and R2 may be bonded to each other and form a ring.) R3 indicates an n-valent group selected from the group comprising a hydrogen atom and a substituted or un-substituted hydrocarbon group, n being an integer from 1 to 10.).

On the addition of lithiated 2-alkyl- and 2-(chloroalkyl)-4,5-dihydro-1,3-oxazoles to nitrones - A mechanistic investigation

The addition of 2-(lithioalkyl)-4,5-dihydro-1,3-oxazoles 2a-c and 2-[chloro(lithio)alkyl]-4,5-dihydro-1,3-oxazoles 2d,e to nitrones 3 has been studied. While lithiated 2-methyl-4,5-dihydro-1,3-oxazole 2a adds stereoselectively to nitrones 3, resulting after long reaction times (3 h) in the formation of 2-[(E)-alkenyl]-4,5-dihydro-1,3-oxazoles 8a-h, lithiated 2-(chloromethyl)-4,5-dihydro-1,3-oxazole 2e affords 2-[(Z)-alkenyl]-4,5-dihydro-1,3-oxazoles 26a-d and 26f-h. α-Lithiated 2-ethyl-4,5-dihydro-1,3-oxazole 2b adds to 3a to give the 1,6-dioxa-2,9-diazaspiro[4.4]nonane 9 and 2-alkenyl-4,5-dihydro-1,3-oxazole 14 after treatment with oxalic acid. Quenching after short reaction times shows that the conversions of 2a to 8 and of 2b to 14 go through spirocyclic compounds 7 and 9, while the reaction between 2e and 3a, quenched even at short reaction times, gives a mixture of the 1,6-dioxa-2,9-diazaspiro[4.4]nonanes 21-H and 22-H and the 2-(1,2-oxazetidin-4-yl)-4,5-dihydro-1,3-oxazoles 25a and 27a. The addition of 2c to 3a furnishes the 1,6-dioxa-2,9-diazaspiro-[4.4]nonane 15 and then isoxazolidin-5-one 16 upon hydrolysis with oxalic acid. The addition of 2d to 3a gives the 1,6- dioxa-2,9-diazaspiro[4.4]nonanes 17b and 18b after short reaction times and the 2-(1,2-oxazetidin-4-yl)-4,5-dihydro-1,3-oxazole 19 after long reaction times. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Electron Paramagnetic Resonance Study of Imine Radical Cations in Low-temperature Solid Matrices

A series of imine radical cations has been studied by EPR spectroscopy, generated in low-temperature halogenocarbon matrices by γ-radiolysis.Radicals of the type ArCH=NR.+ tend to be formed in the 2A'state, corresponding to ionisation of the in-plane (mainly the nitrogen lone-pair) a' orbital (I).These are isostructural with the corresponding vinyl radicals and show angular geometries at the radical centres and large couplings (ca. 85 G) to the proton trans to the nominally nitrogen-localised SOMO (I).When R = But, a 12 G long-range coupling is observed to a single proton from the But group, arising via the W-configuration (II).This coupling was found to persist in the CFCl3 matrix up to its melting point (ca. 160 K), but was lost reversibly in the higher melting CCl4 matrix at ca. 200 K. When R = phenyl, the radical centre is rendered linear, because of the partial ?-bonding between the aromatic ring and the nitrogen atom due to delocalisation of the unpaired electron, as shown by a fall in the parallel (14N) coupling with a concomitant increase in the nitrogen 2p/2s ratio, and by the observation of couplings to the ortho and para phenyl protons. For imines derived from benzophenone (Ph2C=NR) the tendency is for ionisation to occur from the ?-orbital (III) which has large spin densities on the para carbon atoms. Benzophenone imine (Ph2C=NH), in addition to forming the ?-state (III), was found to deprotonate, giving rise to the Ph2C=N. radical.Similar behaviour was shown by benzophenone oxime, which gave only the corresponding iminoxyl radical (Ph2C=N-O.), and we propose that this is due to the dissolution of the latter two materials in the form of hydrogen-bonded molecular clusters in the non-polar freon solvent, thus facilitating deprotonation of the primary cations.