McFadyen–Stevens reaction

The McFadyen–Stevens reaction is a chemical reaction best described as a base-catalyzed thermal decomposition of acylsulfonylhydrazides to aldehydes.^[1][2]

Dudman et al. have developed an alternative hydrazide reagent.^[3]

Reaction mechanism

The mechanism of the McFadyen–Stevens reaction is still under investigation. Two groups have independently proposed a heterolytic fragmentation mechanism.^[4][5] The mechanism involves the deprotonation of the acyl sulfonamide followed by a 1,2-hydride migration to give the alkoxide (3). The collapse of the alkoxide results in the fragmentation producing the desired aldehyde (4),

Martin et al. have proposed a different mechanism involving an

• Hydrazide

References

1. doi:10.1039/jr9360000584
   .
2. ISBN 0471264180
   .
3. doi:10.1016/0040-4039(80)80096-7
   .
4. doi:10.1039/jr9580001843
   .
5. PMID 13807198
   .
6. doi:10.1021/jo00929a600
   .