Not to be confused with Stephen aldehyde synthesis.
The Stevens rearrangement in organic chemistry is an organic reaction converting quaternary ammonium salts and sulfonium salts to the corresponding amines or sulfides in presence of a strong base in a 1,2-rearrangement.[1]
Stevens rearrangement overview
The reactants can be obtained by alkylation of the corresponding amines and sulfides. The substituent R next the amine methylene bridge is an electron-withdrawing group.
The original 1928 publication by Thomas S. Stevens[2] concerned the reaction of 1-phenyl-2-(N,N-dimethylamino)ethanone with benzyl bromide to the ammonium salt followed by the rearrangement reaction with sodium hydroxide in water to the rearranged amine.
Stevens rearrangement 1928
A 1932 publication[3] described the corresponding sulfur reaction.
^Pine SH (2011). The Base-Promoted Rearrangements of Quaternary Ammonium Salts. Organic Reactions. pp. 403–464. doi:10.1002/0471264180.or018.04. ISBN 978-0471264187. {{cite book}}: |journal= ignored (help)
^Stevens TS, Creighton EM, Gordon AB, MacNicol M (1928). "CCCCXXIII.—Degradation of quaternary ammonium salts. Part I". J. Chem. Soc.: 3193–3197. doi:10.1039/JR9280003193.
^Stevens, T.S.; et al. (1932). "8. Degradation of quaternary ammonium salts. Part V. Molecular rearrangement in related sulphur compounds". J. Chem. Soc.: 69. doi:10.1039/JR9320000069.
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