139748-22-4

Upstream product

• 144-86-5 N-chloro-4-methylbenzenesulfonamide 
• 932-89-8 2-cyclohexylidene ethanol 
• 139748-21-3 4-methyl-N-(1-(oxiran-2-yl)cyclohexyl)benzenosulfonamide 

Downstream Products

• 909794-66-7 2,2-cyclohexyl-1-tosylpyrrolidin-3-ol 
• 139748-21-3 4-methyl-N-(1-(oxiran-2-yl)cyclohexyl)benzenosulfonamide 

Relevant academic research and scientific papers

Synthesis of N-heterocycles, beta-amino acids, and allyl amines via aza-payne mediated reaction of ylides and hydroxy aziridines

An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under the basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring closure yields the desired pyrrolidine, thus completing the relay of the 3-membered the 5-membered nitrogen containing ring system. This process takes place with complete transfer of stereochemical fidelity, and can be applied to sterically hindered aziridinols.

Payne-Like Rearrangement of N-Tosyl-Oxiranemethylamines: A New Route to Functionalized Aziridines.

The reaction of N-tosyl-oxiranemethylamines with aqueous sodium hydroxide affords N-tosyl-aziridinemethanols in excellent yields, through the intramolecular epoxide ring opening by the nitrogen atom of the tosylamino group. Key Words: Oxiranemethylamines;