This MedLibrary.org supplementary page on McFadyen-Stevens reaction is provided directly from the open source Wikipedia as a service to our readers. Please see the note below on authorship of this content, as well as the Wikipedia usage guidelines. To search for other content from our encyclopedia supplement, please use the form below:
Related Sponsors
The McFadyen-Stevens reaction is a chemical reaction best described as a base-catalyzed thermal decomposition of acylsulfonylhydrazides to aldehydes.
Dudman has developed an alternative hydrazide reagent.
Reaction mechanism
The mechanism of the McFadyen-Stevens reaction is still under investigation. Two groups have independently proposed a heterolytic fragmentation mechanism. The mechanism involves the deprotonation of the acyl sulfonamide followed by a 1,2-proton migration to give the alkoxide (3). The collapse of the alkoxide results in the fragmentation producing the desired aldehyde (4), nitrogen gas, and an aryl sulfinate ion (5).
Martin et al. have proposed a different mechanism involving an acyl nitrene.
References
- ^ McFadyen, J. S.; Stevens, T. S. J. Chem. Soc. 1936, 584.
- ^ Mosettig, E. Org. React. 1954, 8, 232-240. (Review)
- ^ Dudman, C. C. et al. Tetrahedron Lett. 1980, 4645.
- ^ Brown, V. M.; Carter, P. H.; Tomlinson, M. J. Chem. Soc. 1958, 1843.
- ^ Campaigne, E.; Thompson, R. L.; Van Werth, J. E. J. Med. Chem. 1959, 1, 577.
- ^ Martin, S. B.; Craig, J. C.; Chan, R. P. K. J. Org. Chem. 1974, 39, 2285 - 2289. (doi:10.1021/jo00929a600)
See also
Wikipedia content modification information:
- This page was last modified on 25 June 2008, at 15:40.
Wikipedia Authorship and Review
Wikipedia content provided here is not reviewed directly by MedLibrary.org. Wikipedia content is authored by an open community of volunteers and is not produced by or in any way affiliated with MedLibrary.org.
Wikipedia Usage Guidelines
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article on "McFadyen-Stevens reaction".
The URL for this specific entry is:
All Wikipedia text is available under the terms of the GNU Free Documentation License. (See Copyrights for details). Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc.