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Mercury derivatives of α-diazo ketones

✍ Scribed by Peter Yates; François X. Garneau

Book ID
104224087
Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
170 KB
Volume
8
Category
Article
ISSN
0040-4039

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✦ Synopsis

Oxidation of the monohydrazones of a-diketones with yellow mercuric oxide in the presence of base is a weil-known method for the preparation of a-diazo ketones (1). Some years ago, the interestinq observation was made (2) that when this reaction was applied to I, the hydrazone of an a-ketoaldehyde, the crude product showed in its infrared spectrum two bands in the "diazo stretching" region [4.7 -5.0 p (3)]. One of these (4.76 u) was shown to be due to the expected product, the a-diazo ketone II, but the nature of the product givins rise to the second band (4.82 II) was not determined. It was found, however, that this second product was not formed when I was oxidi--th activated manganese dioxide (4), RCOCH=NNHz RCOCHNz I, R = 2,4,6-(CH3)3C6Hz II, R = 2,4r6-(CH3)3C6H2

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The Wolff rearrangement of α-acetoxy dia
The Wolff rearrangement of α-acetoxy diazo ketones
✍ F.W. Bachelor; G.A. Miana 📂 Article 📅 1967 🏛 Elsevier Science 🌐 French ⚖ 156 KB

The Wolff rearrangement of a-diazo ketones to prepare homologous acids or their derivatives has not been generally applied to the preparation of B-acetoxy acids. We have attempted to use this reaction to accomplish such a transformation but find that the major products are those resulting from g-eli