14033-75-1

Upstream product

• 63089-64-5 2-(4-tert-butyl-1-cyclohexenyl)-2-methylpropiononitrile 
• 64042-37-1 4-tert-Butyl-1-[1-methyl-1-(phenylseleno)-ethyl]-cyclohexanol 
• 53230-01-6 C₉H₁₁LiSe 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 67-64-1 acetone 
• 63089-67-8 4-tert-butyl-1-isopropylcyclohexene 
• 83587-43-3 P-isopropyl-N,N-dimethyl-P-phenylphosphinothioic amide 
• 19437-28-6 1-isopropyl-4-tert-butyl cyclohexanol(eq) 
• 104332-00-5 4-t-butyl-1-(1'methyl-1'-methylseleno)-ethyl-cyclohexane-1-ol 
• 14252-46-1 2,2-bis(phenylthio)propane 
• 63089-63-4 1-(α-Cyanoaethyliden)-4-t-butylcyclohexan 

Downstream Products

• 58976-72-0 trans-1-Isopropyl-4-t-butyl-cyclohexan 
• 30127-32-3 cis-1-Isopropyl-4-t-butyl-cyclohexan 
• 521275-50-3 4-tert-butyl-1-isopropenylcyclohexyl hydroperoxide 
• 98-53-3 4-tercbutyl-cyclohexanone 

Relevant academic research and scientific papers

Oxidative Cleavage of Alkenes by O2with a Non-Heme Manganese Catalyst

The oxidative cleavage of C═C double bonds with molecular oxygen to produce carbonyl compounds is an important transformation in chemical and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C═C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atmospheric pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asymmetric, mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.

Regioselective radical cyclization initiated by the reaction of allylic hydroperoxides with iron(II) sulfate

Treatment of 1-methyl-2-methylene-1-cyclohexyl hydroperoxide with a mixture of FeSO4/CuCl2 yielded 1-(1-chlorocyclohexyl)ethanone as the major product consistent with 6-endo-trig cyclization of the intermediate 5-acetylhex-5-enyl rad

Stereoselective acetalization of 1,3-alkanediols controlled by intramolecular van der Waals attractive interactions and its application to an enantiodifferentiating transformation of σ-symmetric 1,3,5-pentanetriols

Acetalization reactions of racemic bis(trimethylsilyl) ethers (R1R2CHCH(OTMS)CH(R3)CH2OTMS) with racemic menthone, under thermodynamically controlled conditions, stereoselectively give spiroacetal 2 (in which the substituent R1R2CH- is attached to the carbon adjacent to the axial oxygen atom with respect to the menthane ring) in preference to the diastereomeric spiroacetal 3 (in which the substituent is attached to the carbon adjacent to the equatorial oxygen atom). Correlation between the stereoselectivities and the structures of the spiroacetals as well as the higher stereoselectivities observed in the related acetalization with 7,7,7-trimethylmenthone indicates that the preferential formation of spiroacetal 2 of a folded structure is a result of intramolecular attractive interactions between the menthane moiety and the substituent attached to the 1,3-dioxane ring. Molecular mechanics (MM2) calculations give satisfactory agreement with experiments and provide support for the operation of the van der Waals attractive interaction as the most important factor determining the stereoselectivities. The stereoselective acetalization with l-menthone is successfully applied to a novel enantiodifferentiating transformation of σ-symmetric 1,3,5-pentanetriols (HOCH2CHRCH(OH)CHRCH2OH; R = Me or H). The reaction provides an efficient and straightforward route to chiral menthonide derivatives 13a-c, which can be utilized as versatile chiral building blocks.

STEREOCHEMICAL OUTCOME OF THE REACTION OF SOME α-SELENOALKYLLITHIUMS WITH 4-t-BUTYL CYCLOHEXANONE

α-selenoalkyllithiums were found to have a high propensity to add to 4-t-butyl cyclohexanone in an equatorial mode.Stereochemical assignments are discussed.