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Chemistry · Glossary

What is Isocyanates, Curtius and Hofmann rearrangements?

Also known as: isocyanate · Curtius rearrangement · Hofmann rearrangement

Definition 27.21 University Chemistry — Year 3 · Chapter 27 — Radicals, Carbenes and Rearrangements

An isocyanate is a compound R−N=C=O\ce{R-N=C=O}. In the Curtius rearrangement an acyl azide loses dinitrogen on heating while the R group moves from carbon to nitrogen, giving an isocyanate; in the Hofmann rearrangement a primary amide treated with bromine and base gives the same isocyanate through an N-bromoamide. With water the isocyanate gives the amine RNHX2\ce{RNH2} and carbon dioxide; with an alcohol, a carbamate.

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