Citation: Hongyu Cheng, Ruiyao Wang, Xingwen Sun. Mechanistic Study of the Classic Hofmann Elimination Reaction[J]. University Chemistry, ;2025, 40(12): 187-191. doi: 10.12461/PKU.DXHX202510104 shu

Mechanistic Study of the Classic Hofmann Elimination Reaction

1.
Department of Chemistry, Fudan University, Shanghai 200433, China;
2.
High School Affiliated to Fudan University, Shanghai 200433, China

Corresponding author: Xingwen Sun, sunxingwen@fudan.edu.cn
Received Date: 29 October 2025
Revised Date: 3 December 2025

This paper evaluates the mechanisms of the classic Hofmann elimination, especially the elimination reaction of cyclic quaternary ammonium hydroxide. When there are two trans-coplanar β-H, the hydrogen on the carbon with more substituents tends to be eliminated, resulting in the main product being an olefin with Zaitsev selectivity. This conclusion is also supported by DFT study result.
- Quaternary ammonium hydroxide,
- Hofmann elimination,
- Zaitsev selectivity,
- Hofmann selectivity
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沈阳化工大学材料科学与工程学院沈阳 110142