Synthesis and Reactivity Study of Two New Dihydroisoquinoline-Derived Oxaziridines

Abstract

The N-alkyl oxaziridines may be used as reagents for the oxidation of sulfides in acid-promoted reactions. The present work describes the behavior of two newly synthesized dihydroisoquinoline-derived oxaziridines with respect to methanesulfonic acid. An isomerization reaction was observed in the absence of sulfide.

Keywords:

• Hydroxamic acid
• methanesulfonic acid
• nitrone
• oxaziridine
• oxygen transfer

Notes

^a Reaction performed at room temperature in CH₂Cl₂.

^b 0.5 mmol of sulfide (0,16 M), 2 equivalent of MsOH, and 1 equivalent of oxaziridine.

^c Determined by TLC.

^d Determined by ¹H NMR spectroscopy in CDCl₃.

^e Isolated product.