51411-38-2

Upstream product

• 250650-63-6 N-diphenylmethylcyclohexylmethylamine 
• 119-61-9 benzophenone 
• 1013-88-3 Benzophenone imine 
• 50877-01-5 cyclohexanmethylamine hydrochloride 
• 3218-02-8 cyclohexylmethylamine 
• 2043-61-0 cyclohexanecarbaldehyde 
• 91-00-9 Benzhydrylamine 
• 169698-49-1 (E)-N-(cyclohexylmethylene)-1,1-diphenylmethanamine 

Downstream Products

• 50877-01-5 cyclohexanmethylamine hydrochloride 
• 1262639-81-5 1-cyclohexyl-N-(diphenylmethylidene)but-3-en-1-amine 
• 1262639-80-4 N-(cyclohexylmethyl)-1,1-diphenylbut-3-en-1-amine 
• 3218-02-8 cyclohexylmethylamine 

Relevant academic research and scientific papers

Tropylium ion mediated α-cyanation of amines

Tropylium ion mediated α-cyanation of amines is described. Even in the presence of KCN, tropylium ion is capable of oxidizing various amine substrates, and the resulting iminium ions undergo salt metathesis with cyanide ion to produce aminonitriles. The byproducts of this transformation are simply cycloheptatriene, a volatile hydrocarbon, and water-soluble potassium tetrafluoroborate. Thirteen total substrates are shown for the α-cyanation procedure, including a gram scale synthesis of 17β-cyanosparteine. In addition, a tropylium ion mediated oxidative aza-Cope rearrangement is demonstrated.

Oxidative deprotection of diphenylmethylamines

(formula presented) The diphenylmethyl amino protecting group can be efficiently removed by initial oxidation of the amine to an imine by 2,3-dichloro-5,6-dicyanobenzoquinone. The resulting imine can then be easily hydrolyzed under mildly acidic conditions. This method is particularly well suited for the preparation of α-amino phosphinates and α-amino phosphonates.

Efficient transamination under mild conditions: Preparation of primary amine derivatives from carbonyl compounds via imine isomerization with catalytic amounts of potassium tert-butoxide

1,3-Prototropic rearrangement of N-diphenylmethanimines was successfully performed with a catalytic amount of potassium tert-butoxide. This procedure can also be used with aliphatic and aromatic aldimines and was extended to the isomerization of (1R)-camphorquinone monoimine and N-(4-methoxyphenyl)-4-phenyl-3-iminoazetidin-2-one. The isomerized imines were easily hydrolyzed and isolated as Cbz derivatives.