The Curtius rearrangement, as first defined by Theodor Curtius, is a chemical reaction that involves the rearrangement of an acyl azide to a isocyanate. Geheimrat Professor Dr. Julius Wilhelm Theodor Curtius was professor of Chemistry on Heidelberg University and others. ... A chemical reaction is a process that results in the interconversion of Chemical substances . ... Acyl is an organic radical (or functional group) obtained from an organic acid by the removal of the carboxylic hydroxyl group. ... An azide is a N3- anion, or a reactive group in organic chemistry where a carbon substituent is attached as RN3. ... Isocyanate is the chemical group of atoms -N=C=O (1 nitrogen, 1 carbon, 1 oxygen), as opposed to cyanate, -O-C≡N, which is formed from cyanogen in the normal -ate manner. ...

The isocyanate can be trapped by a variety of nucleophiles. Often water is added to hydrolyze the isocyanate to an amine. When done in the presence of tert-butanol, the reaction generates BOC-protected amines, useful intermediates in organic synthesis.^[1][2] Image File history File links Download high resolution version (878x197, 2 KB) Summary Description: Reaction scheme of the Curtius rearrangement. ... In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ... Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. ... Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ... Butanol is a higher alcohol with a 4 carbon atoms and a general formula of C4H10O. There are 4 different isomeric structures for butanol: butan-1-ol CH3-CH2-CH2-CH2-OH butan-2-ol CH3-CH2-CH(OH)-CH3 sec-butanol CH3-CH-CH3 | CH2OH OH | tert-butanol CH3... BOC has a number of possible meanings: The BOC Group, a multi-national industrial gas company. ... A Protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction. ... Organic synthesis is the construction of organic molecules via chemical processes. ...

Carboxylic acids 1 can be easily converted to acyl azides 3 using diphenylphosphoryl azide 2.^[3][4][5] Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH. In general, the salts and anions of carboxylic acids are called carboxylates. ...

Image File history File links Download high resolution version (1985x494, 6 KB) Summary Description: Using diphenylphosphorylazide to convert an acid to a BOC-protected amine. ...

References

1. ^  Ende, D. J. a.; DeVries, K. M.; Clifford, P. J.; Brenek, S. J. Org. Proc. Res. Dev. 1998, 2, 382-392.
2. ^  Lebel, H.; Leogane, O.; Org. Lett. 2005, 7(19), 4107-4110.
3. ^  Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203-6205.
4. ^  Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151-2157.
5. ^  Wolff, O.; Waldvogel, S. R. Synthesis 2004, 1303-1305.

The Journal of the American Chemical Society (usually abbreviated as , or JACS), is a peer-reviewed scientific journal, published since 1879 by the American Chemical Society. ... Tetrahedron is an international journal publishing full origonal research papers in the field of organic chemistry. ...

General references

• Curtius, T. Ber. 1890, 23, 3023.
• Curtius, T. J. Prakt. Chem. 1894, 50, 275.
• Smith, P. A. S. Org. React. 1946, 3, 337-449.
• Scriven, E. F.; Turnbull, K.; Chem. Rev. 1988, 88, 297-368.

Chemische Berichte (usually abbreviated as or ) is a German-language scientific journal featuring chemistry of all disciplines. ... Chemical Reviews (usually abbreviated as ), is a peer-reviewed scientific journal, published since 1900 by the American Chemical Society. ...

See also

• Schmidt reaction