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An Air-Stable Alkene-Derived Organic Radical Cation.

ABSTRACT: Alkenes are known to undergo oxidation to radical cations and dications. The radical cations are often highly reactive and not stable under air. Herein, we report the synthesis, isolation, characterization, and molecular structure of an alkene-derived radical cation A, which is stable in air both in the solid state and in solution. The access to this compound was facilitated from E-diamino tri-substituted alkene B as a synthon for the synthesis of A through one-electron oxidation. The E-diamino tri-substituted alkene B was synthesized by the two-electron reduction of N,N'-1,2-propylene-bridged bis-2-phenyl-pyrrolinium cation C. Under two-electron oxidation, alkene B transforms back to cation C involving a double carbocation rearrangement.

SUBMITTER: Kumar R

PROVIDER: S-EPMC8757455 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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An Air-Stable Alkene-Derived Organic Radical Cation.

Kumar Rahul R Chandra Shubhadeep S Nayak Mithilesh Kumar MK Singha Hazari Arijit A Elvers Benedict J BJ Schulzke Carola C Sarkar Biprajit B Jana Anukul A

ACS omega 20211223 1

Alkenes are known to undergo oxidation to radical cations and dications. The radical cations are often highly reactive and not stable under air. Herein, we report the synthesis, isolation, characterization, and molecular structure of an alkene-derived radical cation A, which is stable in air both in the solid state and in solution. The access to this compound was facilitated from E-diamino tri-substituted alkene B as a synthon for the synthesis of A through one-electr ...[more]

PMID: 35036750

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