PhI(OAc)2 Oxidative Dearomatization of o-Methoxy-phenols. A Facile Preparation of ortho-endo bicyclo[2.2.2]octenones

Christos Anagnostopoulos; Christos Kalogiros; Maria Nikolaidou; Leandros V. Polychronis; Eirini Tileli; Lazaros P. Hadjiarapoglou

doi:10.3762/bxiv.2026.34.v1

PhI(OAc)₂ Oxidative Dearomatization of o-Methoxy-phenols. A Facile Preparation of ortho-endo bicyclo[2.2.2]octenones

Christos Anagnostopoulos ,
Christos Kalogiros ,
Maria Nikolaidou ,
Leandros V. Polychronis ,
Eirini Tileli and
Lazaros P. Hadjiarapoglou

Submitting author affiliation:

Department of Chemistry, University of Ioannina, Ioannina, Greece

Beilstein Arch. 2026, 202634. https://doi.org/10.3762/bxiv.2026.34.v1

Published 16 Sep 2026

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Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Abstract

Diels-Alder cycloadditions of 6-allyl-2,2-dimethoxycyclohexa-3,5-dienones with dienophiles furnished functionalized ortho-endo bicyclo[2.2.2]octenones with absolute regio-and stereoselectivity. The competition between self-dimerization and cycloaddition with an external dienophile exists, but the retro-Diels-Alder/Diels-Alder sequence favors the formation of the cycloadducts.

Keywords: masked o-benzoquinones; Diels-Alder ; o-methoxyphenol ; (diacetoxy)iodobenzene oxidation

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Anagnostopoulos, C.; Kalogiros, C.; Nikolaidou, M.; Polychronis, L. V.; Tileli, E.; Hadjiarapoglou, L. P. Beilstein Arch. 2026, 202634. doi:10.3762/bxiv.2026.34.v1

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)