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Org Lett. 2012 Sep 7;14(17):4470-3. doi: 10.1021/ol3019709. Epub 2012 Aug 10.

Validation of diethoxyphosphonate as an effective agent for charge transfer in Anion Relay Chemistry (ARC).

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  • 1Department of Chemistry, Laboratory for Research on the Structure of Matter, and the Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.


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.

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