Related Experiment Video
Updated: May 19, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
Published on: November 22, 2016
Validation of diethoxyphosphonate as an effective agent for charge transfer in Anion Relay Chemistry (ARC)
Alexander Sokolsky1, Amos B Smith
1Department of Chemistry, Laboratory for Research on the Structure of Matter, and the Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Abstract:
The diethoxyphosphonate group comprises an effective agent to achieve negative charge migration in Type II Anion Relay Chemistry (ARC). The process involves a [1,4]-phosphorus-Brook rearrangement that proceeds via a phosphacyclic intermediate leading to an anion that can be captured by reactive electrophiles. In the absence of an exogenous electrophile, the anion derived via phosphorus migration undergoes internal displacement of the phosphonate group to produce a diastereomeric mixture of cyclopropanes.
Related Concept Videos
EDTA: Chemistry and Properties
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Ion Exchange
Diazonium Group Substitution: –OH and –H
