123552-88-5

Upstream product

• 138711-63-4 N-(2-bromophenyl)-4-methylbenzenesulfinamide 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 615-36-1 2-bromoaniline 

Downstream Products

• 138711-65-6 C₁₆H₁₆BrNOS 
• 123552-94-3 C₁₅H₁₆BrNOS 

Relevant academic research and scientific papers

Synthesis, deprotonation, and alkylation of S-allyl sulfoximines

N-Phenyl-S-(4-methylphenyl)-sulfoximidoyl chloride 1 reacts with allyltrimethylsilane in the presence of aluminum chloride to give benzothiazine 4 in fair yield along with a small amount of S-allyl sulfoximine 3a. On the other hand, 1 reacts with allyltributyltin to give the S-allyl sulfoximine 3a almost exclusively. This latter reaction appears to be general. The sulfoximine 3a is thermally stable and can be deprotonated smoothly with n-BuLi. The anion reacts regioselectively but not stereoselectively with simple alkylating agents. Reactions of the anion with selected aldehydes and enones proceeds with some regiocontrol and, with some exceptions, little stereocontrol.

A NEW SULFOXIMINE SYNTHESIS

Selected sulfonimidoyl halides react with ethylaluminum dichloride to give S-ethyl sulfoximines in good yields.