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

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

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 oc...

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Veröffentlicht in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 1993-11, Vol.84 (1-4), p.55-61
Hauptverfasser: Serves, Spyros V., Nikolaidou, Viky, Sotiropoulos, Demetrios N., Ioannou, Panayiotis V.
Format: Artikel
Sprache:eng
Schlagworte:
Chemical reactivity
Chemistry
diamines
ephedrine
Exact sciences and technology
L-amino alcohols
mechanism
Organic chemistry
Perkow reaction
Reactivity and mechanisms
Spin labelling
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Zusammenfassung: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.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426509308034315