Donor-Acceptor-Acceptor 1,3-Bisdiazo Compounds: An Exploration of Synthesis and Stepwise Reactivity

Dylan J. Abrams; Huw M.L. Davies; Erik J. Sorensen

doi:10.1021/acs.orglett.0c00103

Donor-Acceptor-Acceptor 1,3-Bisdiazo Compounds: An Exploration of Synthesis and Stepwise Reactivity

Dylan J. Abrams, Huw M.L. Davies, Erik J. Sorensen

Chemistry

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Metal carbenes, derived from the decomposition of diazo compounds, are valued for their capacity to perform a variety of transformations. A unique class of acyclic, bis-diazo compounds, the donor-acceptor-acceptor 1,3-bisdiazo compounds, are described herein. These compounds are available from acyclic β-keto esters and especially reactive at the donor-acceptor diazo unit. These bisdiazo compounds react smoothly with rhodium acetate and alcohols to give monodiazo, cyclic orthoesters, presumably through the capture of a transient oxonium ylide.

Original language	English (US)
Pages (from-to)	1791-1795
Number of pages	5
Journal	Organic letters
Volume	22
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.0c00103
State	Published - Mar 6 2020

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c00103

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abstract = "Metal carbenes, derived from the decomposition of diazo compounds, are valued for their capacity to perform a variety of transformations. A unique class of acyclic, bis-diazo compounds, the donor-acceptor-acceptor 1,3-bisdiazo compounds, are described herein. These compounds are available from acyclic β-keto esters and especially reactive at the donor-acceptor diazo unit. These bisdiazo compounds react smoothly with rhodium acetate and alcohols to give monodiazo, cyclic orthoesters, presumably through the capture of a transient oxonium ylide.",

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AU - Sorensen, Erik J.

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AB - Metal carbenes, derived from the decomposition of diazo compounds, are valued for their capacity to perform a variety of transformations. A unique class of acyclic, bis-diazo compounds, the donor-acceptor-acceptor 1,3-bisdiazo compounds, are described herein. These compounds are available from acyclic β-keto esters and especially reactive at the donor-acceptor diazo unit. These bisdiazo compounds react smoothly with rhodium acetate and alcohols to give monodiazo, cyclic orthoesters, presumably through the capture of a transient oxonium ylide.

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Donor-Acceptor-Acceptor 1,3-Bisdiazo Compounds: An Exploration of Synthesis and Stepwise Reactivity

Abstract

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