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

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.

SUBMITTER: Sokolsky A

PROVIDER: S-EPMC3439805 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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

Sokolsky Alexander A Smith Amos B AB

Organic letters 20120810 17

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 cyclo ...[more]

PMID: 22880799

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