Tetrahedron

The regio-and stereochemistry of the alkoxide-induced ring-opening of methoxymethylidene-substituted homopthalic anhydride

MG Hutchings, AM Chippendale, I Ferguson

Index: Hutchings, Michael G.; Chippendale, A. Margaret; Ferguson, Ian Tetrahedron, 1988 , vol. 44, # 12 p. 3727 - 3734

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Citation Number: 17

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-nmr 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 ...