Oxidative Rearrangement via 1,2-Aryl Migration using Hydroxy(tosyloxy)iodobenzene in a Polar Aprotic Solvent

Raj Kamal; Vipan Kumar; Ravinder Kumar; Sangeeta Saini; Rajesh Kumar

doi:10.1055/s-0040-1708010

Synlett, Table of Contents

Synlett 2020; 31(10): 959-964
DOI: 10.1055/s-0040-1708010

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Oxidative Rearrangement via 1,2-Aryl Migration using Hydroxy(tosyloxy)iodobenzene in a Polar Aprotic Solvent

Raj Kamal ∗

^aDepartment of Chemistry, Kurukshetra University, Kurukshetra, Haryana 136119, India Email: kamalraj_sharma@rediffmail.com

,

Vipan Kumar

^aDepartment of Chemistry, Kurukshetra University, Kurukshetra, Haryana 136119, India Email: kamalraj_sharma@rediffmail.com

,

Ravinder Kumar

^aDepartment of Chemistry, Kurukshetra University, Kurukshetra, Haryana 136119, India Email: kamalraj_sharma@rediffmail.com

,

Sangeeta Saini

^aDepartment of Chemistry, Kurukshetra University, Kurukshetra, Haryana 136119, India Email: kamalraj_sharma@rediffmail.com

,

Rajesh Kumar

^bDepartment of Chemistry, Mukand Lal National College, Yamuna Nagar, Haryana 135001, India

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Abstract

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Abstract

A series of geminal β,β-ditosyloxy ketones were synthesized in moderate to good yields through hydroxy(tosyloxy)iodobenzene-mediated ditosyloxylation of readily accessible α,β-unsaturated ketones in a polar aprotic solvent. A mechanism has been proposed for the synthesis of the geminal β,β-ditosyloxy ketones, and entails an oxidative rearrangement involving a 1,2-aryl migration.

Key words

aryl migration - ditosyloxylation - ditosyloxy ketones - hypervalent iodine - rearrangement

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References

References and Notes
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