80053-69-6

Basic information

• Product Name: Cyclohexanone, O-(methylsulfonyl)oxime
• CAS NO: 80053-69-6
• Molecular Formula: C7H13NO3S
• Molecular Weight: 191.251
• Mol File: 80053-69-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, O-(methylsulfonyl)oxime(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, O-(methylsulfonyl)oxime(80053-69-6)
• EPA Substance Registry System: Cyclohexanone, O-(methylsulfonyl)oxime(80053-69-6)

Safety Data

• Hazardous Substances Data: 80053-69-6(Hazardous Substances Data)

Upstream product

• 108-94-1 cyclohexanone 
• 100-64-1 cyclohexanone-oxime 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 86921-56-4 2-Methyl-2-(4,5,6,7-tetrahydro-3H-azepin-2-yl)-cyclohexanone 
• 86921-55-3 2-Azepan-(2Z)-ylidene-6-methyl-cyclohexanone 
• 13748-14-6 (R*S*)-2-propylazepane hydrochloide 
• 3338-05-4 2-Propyl-1-aza-cyclohept-1-en 
• 4361-44-8 3-cyclohexylpropan-1-amine 
• 54-95-5 pentetrazole 
• 3466-82-8 2-phenylazacycloheptane 
• 80053-55-0 2-Isobutyl-azepane 
• 80053-54-9 2-ethylhexahydro-1H-azepine 
• 84039-87-2 2-n-butylazacycloheptane 

Relevant articles and documents

Atypical and Asymmetric 1,3-P,N Ligands: Synthesis, Coordination and Catalytic Performance of Cycloiminophosphanes

Novel seven-membered cyclic imine-based 1,3-P,N ligands were obtained by capturing a Beckmann nitrilium ion intermediate generated in situ from cyclohexanone with benzotriazole, and then displacing it by a secondary phosphane under triflic acid promotion. These “cycloiminophosphanes” possess flexible non-isomerizable tetrahydroazepine rings with a high basicity; this sets them apart from previously reported iminophophanes. The donor strength of the ligands was investigated by using their P-κ1- and P,N-κ2-tungsten(0) carbonyl complexes, by determining the IR frequency of the trans-CO ligands. Complexes with [RhCp*Cl2]2 demonstrated the hemilability of the ligands, giving a dynamic equilibrium of κ1 and κ2 species; treatment with AgOTf gives full conversion to the κ2 complex. The potential for catalysis was shown in the RuII-catalyzed, solvent-free hydration of benzonitrile and the RuII- and IrI-catalyzed transfer hydrogenation of cyclohexanone in isopropanol. Finally, to enable access to asymmetric catalysts, chiral cycloiminophosphanes were prepared from l-menthone, as well as their P,N-κ2-RhIII and a P-κ1-RuII complexes.

2-Propyl-1-azacycloheptane from cyclohexanone oxime

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Organoaluminum-Promoted Beckmann Rearrangement of Oxime Sulfonates

The Beckmann rearrangement of oxime sulfonates with simultaneous nucleophilic trapping of the intermediary iminocarbocation by organoaluminum reagents is described.This process provides a new and highly efficient route to imino thioethers, imino selenoethers, imino nitriles, and α-alkylated amines starting from oxime sulfonates by the use of dialkylaluminum thiolates, selenolates, diethylaluminum chloride-trimethylsilyl cyanide, and trialkylaluminum-diisobutylaluminum hydride systems, respectively.The present organoaluminum-promoted Beckmann rearrangement of oxime sulfonates has been successfully applied to the synthesis of naturally occuring alkaloids, pumiliotoxin C and solenopsin A and B, in stereoselective fashion.Moreover, α,α-dialkylation of amines can be realized by the successive treatment of oxime sulfonates with trialkylaluminum followed by allylic or propargylic Grignard reagents in synthetically useful yields.