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Synlett 2020; 31(10): 959-964
DOI: 10.1055/s-0040-1708010
letter
© Georg Thieme Verlag Stuttgart · New York

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

Raj Kamal  ∗
a   Department of Chemistry, Kurukshetra University, Kurukshetra, Haryana 136119, India   Email: kamalraj_sharma@rediffmail.com
,
Vipan Kumar 
a   Department of Chemistry, Kurukshetra University, Kurukshetra, Haryana 136119, India   Email: kamalraj_sharma@rediffmail.com
,
Ravinder Kumar
a   Department of Chemistry, Kurukshetra University, Kurukshetra, Haryana 136119, India   Email: kamalraj_sharma@rediffmail.com
,
Sangeeta Saini
a   Department of Chemistry, Kurukshetra University, Kurukshetra, Haryana 136119, India   Email: kamalraj_sharma@rediffmail.com
,
Rajesh Kumar
b   Department of Chemistry, Mukand Lal National College, Yamuna Nagar, Haryana 135001, India
› Author AffiliationsR.K. acknowledges financial assistance as a minor research project from Kurukshetra University (File No. DPA-1/32/13/ARA/3075-78). S.S. thanks the Science and Engineering Research Board (SERB), a statutory body of the Department of Science & Technology (DST), Government of India, for financial assistance under the Young Scientist Scheme (File No. YSS/2014/000555).
Further Information

Publication History

Received: 06 January 2020

Accepted after revision: 08 March 2020

Publication Date:
27 March 2020 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1708010.
  • Supporting Information
 

  • References and Notes

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