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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/3936
Title: Iodobenzene and m-chloroperbenzoic acid mediated oxidative dearomatization of phenols
Authors: Taneja N.
Peddinti, Rama Krishna
Published in: Tetrahedron Letters
Abstract: Oxidative dearomatization of 2- and 4-substituted phenols to their corresponding benzoquinone monoketals by catalytic amount of iodobenzene, and m-CPBA as a co-oxidant has been achieved via in situ generation of PhIO2, a hypervalent iodine(V) species. The transiently generated orthobenzoquinone monoketals further underwent Diels–Alder reaction with various dienophiles to furnish densely substituted bicyclo[2.2.2]octenones in high selectivities and yields. This methodology features ready availability of reagents, cost effectiveness, safety, brevity, selectivity, diversity and excellent yields. © 2016
Citation: Tetrahedron Letters (2016), 57(35): 3958-3963
URI: https://doi.org/10.1016/j.tetlet.2016.07.078
http://repository.iitr.ac.in/handle/123456789/3936
Issue Date: 2016
Publisher: Elsevier Ltd
Keywords: Bicyclo[2.2.2]octenones
Diels–Alder cycloaddition
Linearly conjugated dienones
Orthobenzoquinone monoketals
Oxidative acetalization
ISSN: 404039
Author Scopus IDs: 57190733026
6602375630
Author Affiliations: Taneja, N., Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India
Peddinti, R.K., Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India
Funding Details: This work was supported by DST [research grant No. SR/S1/OC-38/2011 ], New Delhi. We thank DST for providing HRMS facility in FIST program and N.T. thanks MHRD for a research fellowship.
Corresponding Author: Peddinti, R.K.; Department of Chemistry, Indian Institute of Technology RoorkeeIndia; email: rkpedfcy@iitr.ac.in
Appears in Collections:Journal Publications [CY]

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