Rowe rearrangement
The Rowe rearrangement , named after the English chemist Frederick Maurice Rowe , is a name reaction from the field of organic chemistry and was first described in 1926. The Rowe rearrangement offers the possibility of converting pseudo-phthalazinones (also called phthalazin- 1-ones) into phthalazinones (also called phthalazin-4-ones).
Overview reaction
Pseudo-phthalazinones can be rearranged to phthalazinones via an acid-catalyzed reaction under the action of heat:
Reaction mechanism
It is assumed that the aryl group including the nitrogen atom is rearranged. The substituents on the aryl group influence the rate of the reaction. An electron-withdrawing group (e.g. nitro group) favors the reaction, whereas an electron-donating group (e.g. methyl group) delays the reaction. The following mechanism is described in the literature:
Individual evidence
- ^ EH Rodd: Obituary notice: Frederick Maurice Rowe, 1891-1946 In: J. Chem. Soc. 1948, pp. 2323-2330, doi: 10.1039 / JR9480002323 .
- ↑ Frederick Maurice Rowe, Esther Levin, Alan Chamley Burns, John Stanley Herbert Davies and Wolfe Tepper: XCVI. — A new reaction of certain diazosulphonates derived from β-naphthol-1-sulphonic acid. Part I. Preparation of phthalazine, phthalazone, and phthalimidine derivatives from 4'-nitrobenzene-2-naphthol-1-diazosulphonate In: J. Chem. Soc. 129, 1926, pp. 690-706, doi: 10.1039 / JR9262900690 .
- ↑ a b Wyman. R. Vaughan: The Chemistry of the Phthalazines. In: Chem. Rev. 43, 1948, pp. 447-508, doi: 10.1021 / cr60136a003 .
- ^ A b Zerong Wang: Comprehensive Organic Name Reactions and Reagents , Wiley, 2009, ISBN 978-0-471-70450-8 , pp. 2439-2441.