Outline of Contents
- Introduction to Pericyclic Reactions
Reaction classes: Polar v. concerted
Frontier molecular orbitals (FMOs)
- The [4π + 2π] Cycloaddition (Diels-Alder Reaction)
Stereoselectivity and regioselectivity
Substituent effects and Lewis acid catalysis
- Other Concerted [n + m] Cycloadditions
[2 + 2] Processes ('forbidden' and 'allowed' variants)
Other (4n + 2) and (4n) pairings
- Selection Rules and Orbital Symmetry
Introduction to electrocyclic reactions
Conservation of orbital symmetry in the ring-opening of cyclobutene
- Electrocyclic Reactions
Valence tautomerisation processes
- Sigmatropic Rearrangements
[1,5] and [1,7] Hydrogen shifts
[1,3] Sigmatropic shifts
[3,3] Sigmatropic rearrangements
Cope and Claisen rearrangements
Recommended Texts and Support
- J. Clayden, N. Greeves, S. Warren and P. Wothers, Organic Chemistry (Oxford University Press, 2001) ISBN 0198503466 (Ch. 35, 36).
- J. Clayden, N. Greeves and S. Warren, Organic Chemistry 2nd edition (Oxford University Press, 2012) ISBN 0199270295 (Ch. 34, 35).
- I. Fleming, Pericyclic Reactions (Oxford Chemistry Primer, no. 67, 2nd edition) (Oxford University Press, 2015) ISBN 0199680900 (affordable, thorough guidebook).
- I. Fleming, Molecular Orbitals and Organic Chemical Reactions: Student Edition (Wiley-Blackwell, 2009) ISBN 0470746599 (comprehensive reference text).
- The Conservation of Orbital Symmetry: R. B. Woodward and R. Hoffmann, Angew. Chem., Int. Ed. 1969, 8, 781–853.
- A set of molecular models (e.g. Orbit by Cochranes of Oxford) is invaluable.
Background and Acknowledgements
Manchester, July 2018