REACTIONS OF CIS-3,5-DIBROMO-4-OXO-2,2,6,6-TETRAMETHYLPIPERIDIN-1-YLOXY WITH NITROGEN AND PHOSPHORUS NUCLEOPHILES

Abstract

The title free radical can be used to spin label biochemically important amines, but not those which it oxidizes, e.g., epinephrine (adrenaline), and diamines. Product analysis of the reaction between the radical and triethyl phosphite gives evidence that the first step in the Perkow reaction may occur via halogen attack giving enolate bromophosphonium ion pair as the common intermediate.

Key Words:

• Spin labelling
• L-amino alcohols
• ephedrine
• diamines
• Perkow reaction
• mechanism