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Peer-reviewedCC BY-NC-ND 4.0Organic Letters

Acetoxy-Peroxyacetals: A Peroxycarbenium Precursor for the Synthesis of Hydroperoxides and Endoperoxides

  • Yunxin Xing
  • Laurent Ferrié
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Abstract

Herein is examined the reactivity of acetoxy-peroxyacetals as a new source of acyclic peroxycarbenium species. Their reactivity was explored with Sc(OTf)3, a mild Lewis acid that promotes peroxycarbenium species. The resilience of tert-butyldimethylsilyl group on peroxyl function was found superior for substitution reactions, enabling the additions of neutral nucleophiles such as enoxysilanes, silylcyanides, silylazides and allylsilanes. Formal [3+2] cycloaddition proceeds specifically with allyltrimethylsilane, depending on several parameters. Peroxysilanes were ultimately transformed into 1,2-dioxolanes or 1,2-dioxanes in a few steps, thanks to the promotion of a second peroxycarbenium ion, which constitutes a new approach to the synthesis of endoperoxides.

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Cite

BibTeXRIS
BibTeX
@article{xing2026acetoxyperoxyacetals,
  title = {{Acetoxy-Peroxyacetals: A Peroxycarbenium Precursor for the Synthesis of Hydroperoxides and Endoperoxides}},
  author = {Yunxin Xing and Laurent Ferrié},
  journal = {Organic Letters},
  year = {2026},
  month = oct,
  doi = {10.1021/acs.orglett.6c00780},
  url = {https://hal.science/hal-05775188v1},
  note = {CC BY-NC-ND 4.0},
}
RIS
TY  - JOUR
TI  - Acetoxy-Peroxyacetals: A Peroxycarbenium Precursor for the Synthesis of Hydroperoxides and Endoperoxides
AU  - Yunxin Xing
AU  - Laurent Ferrié
PY  - 2026
DA  - 2026/10/02
JO  - Organic Letters
DO  - 10.1021/acs.orglett.6c00780
UR  - https://hal.science/hal-05775188v1
AB  - Herein is examined the reactivity of acetoxy-peroxyacetals as a new source of acyclic peroxycarbenium species. Their reactivity was explored with Sc(OTf)3, a mild Lewis acid that promotes peroxycarbenium species. The resilience of tert-butyldimethylsilyl group on peroxyl function was found superior for substitution reactions, enabling the additions of neutral nucleophiles such as enoxysilanes, silylcyanides, silylazides and allylsilanes. Formal [3+2] cycloaddition proceeds specifically with allyltrimethylsilane, depending on several parameters. Peroxysilanes were ultimately transformed into 1,2-dioxolanes or 1,2-dioxanes in a few steps, thanks to the promotion of a second peroxycarbenium ion, which constitutes a new approach to the synthesis of endoperoxides.
SN  - 1523-7060
SN  - 1523-7052
ER  -