Trimethyl(3-oxido-1-oxoinden-2-yl)ammonium, a New 1,4-Dipolar Ylid

Ernst Horn, Graham P Jones, Rolf H Prager, Michael R Snow, A David Ward

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    Abstract

    Reaction of isobenzofuran-1(3H)-one (phthalide) and its derivatives with dimethylformamide dimethyl acetal in the presence of base gives small amounts (c. 10%)1 of the ylid trimethyl(3- oxido-l-oxomden-2-yl)ammonium (3). The same compound is formed in higher yield from the corresponding 3-dimethylaminomethyleneisobenzofuran-1(3H)-one. Support for this structure comes from chemical degradation and its mode of synthesis, but relies mainly on X-ray crystallography. The title compound crystallizes as clear prisms in the monoclinic space group P21/n with a 15•992(2), b 9•329(4), c 7•112(3) Å, ß 90•15(3)° and Z 4. The structural final refinement of a full-matrix least-squares calculation converged with R 0•044 and Rw 0•045.

    Original languageEnglish
    Pages (from-to)183-187
    Number of pages5
    JournalAustralian Journal of Chemistry
    Volume39
    Issue number1
    DOIs
    Publication statusPublished - 1986

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