85048-06-2

Basic information

• Product Name: (E)-13-Phenylsulfanyl-azacyclotridec-13-ene
• Synonyms: (E)-13-Phenylsulfanyl-azacyclotridec-13-ene
• CAS NO: 85048-06-2
• Molecular Weight: 289.485
• Mol File: 85048-06-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-13-Phenylsulfanyl-azacyclotridec-13-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-13-Phenylsulfanyl-azacyclotridec-13-ene(85048-06-2)
• EPA Substance Registry System: (E)-13-Phenylsulfanyl-azacyclotridec-13-ene(85048-06-2)

Safety Data

• Hazardous Substances Data: 85048-06-2(Hazardous Substances Data)

Upstream product

• 946-89-4 cyclododecanone oxime 
• 36896-63-6 dimethylaluminium phenylthiolate 
• 80053-73-2 C₁₉H₂₉NO₃S 

Relevant articles and documents

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.