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43.8.2.1.5.6 Variation 6: Carbenoid Rearrangement of 3-Nitrosooxazolidin-2-ones and Related Compounds

DOI: 10.1055/sos-SD-043-00415

Krueger, A.Science of Synthesis, (200843491.

3-Nitrosooxazolidin-2-ones 68 can conveniently be obtained from ketones via a Reformatsky reaction, followed by reaction with hydrazine and subsequent coupling with sodium nitrite in hydrochloric acid (Scheme 27).[‌41‌,‌103‌‌106‌] Upon treatment with base, the oxazolidinones 68 isomerize to vinyldiazonium compounds, which lose nitrogen to form the alkynes 69 with migration of one of the substituents in the 5-position.[‌41‌] The mechanism of this reaction is related to the FritschButtenbergWiechell reaction. An intermediate carbene/carbenoid rearranges to the alkyne. The substituents R1 and R2 in the 5-position have an influence on the reaction: only those oxazolidinones that carry substituents with migration ability will isomerize to the respective alkynes.

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