The regio- and stereochemistry of the alkoxide-induced ring-opening of methoxymethylidene-substituted homopthalic anhydride |
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| Institution: | 1. School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, 637459, Singapore;2. School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore;3. Sorbonne Universités, UPMC Univ Paris 06, UMR 8232, Institut Parisien de Chimie Moléculaire, F-75005, Paris, France;4. CNRS, UMR 8232, Institut Parisien de Chimie Moléculaire, F-75005, Paris, France;1. Laboratory of Microbiology, Parasitology and Hygiene (LMPH), Faculty of Pharmaceutical, Biomedical and Veterinary Sciences, University of Antwerp, Universiteitsplein 1, B-2610, Wilrijk, Belgium;2. Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000, Ghent, Belgium;3. Institut de Pharmacologie et de Biologie Structurale (IPBS), Université de Toulouse, CNRS, Université Paul Sabatier, F-31077, Toulouse, France;1. State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China;2. Department of Chemistry, Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055, China |
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| Abstract: | Ring-opening of methoxymethylidene-substituted homophthalic anhydride (1) by methoxide occurs by two modes. Attack at the 1-position (“benzoate” carbonyl) leads to a stable acid-ester. A combination of unambiguous syntheses and 1H- and 13C-n.m.r. spectroscopy has been used to show that this material has the “benzoate ester, acrylic acid” structure (5). This corrects the structure assignment given earlier for this material, which incorrectly concluded “benzoic acid, acrylate ester”, (2). Compound (2), resulting from attack at the “acrylate” carbonyl, is a co-product of (5), but is unstable. It recyclises in an alternative fashion to give (dihydro)isocoumarin-type products (15) and (16). |
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