Diels-Alder reactions of halogenated masked o-benzoquinones: synthesis of halogen-substituted bicyclo[2.2.2]octenones

Seshi Reddy Surasani; Virendra Singh Rajora; Naganjaneyulu Bodipati; Rama Krishna Peddinti

doi:10.1016/j.tetlet.2008.11.117

Diels-Alder reactions of halogenated masked o-benzoquinones: synthesis of halogen-substituted bicyclo[2.2.2]octenones

Seshi Reddy Surasani, Virendra Singh Rajora, Naganjaneyulu Bodipati, Rama Krishna Peddinti

Indian Institute of Technology Roorkee

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

Intermolecular Diels-Alder reactions of 4-halo masked o-benzoquinones generated from hypervalent iodine-mediated oxidation of 4-halo-2-methoxyphenols, with electron-deficient dienophiles-methyl acrylate, methyl methacrylate and methyl vinyl ketone-leading to halo-substituted bicyclo[2.2.2]octenones, are described. The halo-benzoquinone monoketals can be isolated and characterized. The dimerization of these intermediates is not observed under the reaction conditions.

Original language	English
Pages (from-to)	773-775
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2008.11.117
State	Published - 18 Feb 2009
Externally published	Yes

Bibliographical note

Funding Information:
We gratefully acknowledge financial support from the Department of Science and Technology, New Delhi. S.R.S. and N.B. thank CSIR and V.S.R. thanks MHRD, New Delhi, for the award of research fellowships.

Funding

We gratefully acknowledge financial support from the Department of Science and Technology, New Delhi. S.R.S. and N.B. thank CSIR and V.S.R. thanks MHRD, New Delhi, for the award of research fellowships.

Funders	Funder number
Department of Science and Technology, Ministry of Science and Technology, India
Council of Scientific and Industrial Research, India
Ministry of Human Resource Development

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10.1016/j.tetlet.2008.11.117

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abstract = "Intermolecular Diels-Alder reactions of 4-halo masked o-benzoquinones generated from hypervalent iodine-mediated oxidation of 4-halo-2-methoxyphenols, with electron-deficient dienophiles-methyl acrylate, methyl methacrylate and methyl vinyl ketone-leading to halo-substituted bicyclo[2.2.2]octenones, are described. The halo-benzoquinone monoketals can be isolated and characterized. The dimerization of these intermediates is not observed under the reaction conditions.",

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AU - Bodipati, Naganjaneyulu

AU - Peddinti, Rama Krishna

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Diels-Alder reactions of halogenated masked o-benzoquinones: synthesis of halogen-substituted bicyclo[2.2.2]octenones

Abstract

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