Abstract
The Bamford–Stevens reaction and the Shapiro reaction share a similar mechanistic pathway. The former uses a base such as Na, NaOMe, LiH, NaH, NaNH2, heat, etc., whereas the latter employs bases such as alkyllithiums and Grignard reagents. As a result, the Bamford–Stevens reaction furnishes more-substituted olefins as the thermodynamic products, while the Shapiro reaction generally affords less-substituted olefins as the kinetic products.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Bamford, W. R.; Stevens, T. S. M. J. Chem. Soc. 1952, 4735–4740. Thomas Stevens (1900–2000), another chemist centenarian, was born in Renfrew, Scotland. He and his student W. R. Bamford published this paper at the University of Sheffield, UK. Stevens also contributed to another name reaction, the McFadyen–Stevens reaction.
Felix, D.; Müller, R. K.; Horn, U.; Joos, R.; Schreiber, J.; Eschenmoser, A. Helv. Chim. Acta 1972, 55, 1276–1319.
Shapiro, R. H. Org. React. 1976, 23, 405–507. (Review).
Adlington, R. M.; Barrett, A. G. M. Acc. Chem. Res. 1983, 16, 55–59. (Review on the Shapiro reaction).
Chamberlin, A. R.; Bloom, S. H. Org. React. 1990, 39, 1–83. (Review).
Sarkar, T. K.; Ghorai, B. K. J. Chem. Soc., Chem. Commun. 1992, 17, 1184–1185.
Chandrasekhar, S.; Rajaiah, G.; Chandraiah, L.; Swamy, D. N. Synlett 2001, 1779–1780.
Aggarwal, V. K.; Alonso, E.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Porcelloni, M.; Studley, J. R. Angew. Chem. Int. Ed. 2001, 40, 1430–1433.
May, J. A.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 12426–12427.
Zhu, S.; Liao, Y.; Zhu, S. Org. Lett. 2004, 6, 377–380.
Baldwin, J. E.; Bogdan, A. R.; Leber, P. A.; Powers, D. C. Org. Lett. 2005, 7, 5195–5197.
Humphries, P. Bamford–Stevens Reaction. In Name Reactions for Homologations-Part II; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009, pp 642–652. (Review).
Bartrum, H. E.; Blakemore, D. C.; Moody, C. J.; Hayes, C. J. Chem. Eur. J. 2011, 17, 9586–9589.
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Li, J.J. (2014). Bamford–Stevens reaction. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-319-03979-4_8
Download citation
DOI: https://doi.org/10.1007/978-3-319-03979-4_8
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-03978-7
Online ISBN: 978-3-319-03979-4
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)