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Synthesis of 3 : 4-Benztropolone

Nature volume 163, page 410 (1949)Cite this article

Abstract

DEWAR1 has interpreted the chemistry of the mould metabolite, stipitatic acid, and of colchiceine (the methyl ether of which is the alkaloid colchicine) by postulating that they are derived from the hypothetical cycloheptatrienolone (I). This he termed 'tropolone', and he attributed to it quasi-aromatic character. This interesting suggestion, for which no tangible evidence was advanced2, has acquired more plausibility from the recent demonstration of Haworth, Moore and Pauson3 that purpurogallin is a trihydroxybenztropolone, as earlier suggested by Barltrop and Nicholson4, and from the finding of Erdtman and Gripenberg5 that the cedar-wood constituent γ-thujaplicin is an isopropyltropolone. Hitherto, a synthetic tropolone of established constitution has not been prepared, and the properties ascribed to such a structure have been based largely on speculation.

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References

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Authors and Affiliations

  1. Chemistry Department, University of Glasgow,

    J. W. COOK & A. R. SOMERVILLE

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  1. J. W. COOK
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  2. A. R. SOMERVILLE
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COOK, J., SOMERVILLE, A. Synthesis of 3 : 4-Benztropolone. Nature 163, 410 (1949). https://doi.org/10.1038/163410a0

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