Frontier orbital theory and stereoelectronic effects

Course content: Principles that govern the conformation and reactivity of molecules are discussed in terms of stereoelectronic principles and frontier orbital theory. Examples of topics that are dealt with in these contexts are conformational analysis, the anomeric effect, Baldwins's rules for ring-closure, reactions of the carbonyl group, Burgi-Dunitz nucleophilic attack, electrophilic aromatic substitution, Neighboring Group Participation (NGP), non-classical carbocations, ionic rearrangements and fragmentations.

Jerker Mårtensson, jerker@chalmers.se

The following texts contain information pertinent to the course content:

• Clayden, Greeves and Warren, Organic Chemistry, 2nd Edition, Oxford University Press, 2012.
• Alabugin, Stereoelectronic Effects – A bridge between structure and reactivity, Wiley, 2016.
• Fleming, Frontier Orbitals and Organic Chemical Reactions, 1st Edition, Wiley, 1990.
• Fleming, Molecular Orbitals and Organic Chemical Reactions – Reference Edition, Wiley, 2010.
• Kirby, Stereoelectronic Effects, Oxford Chemistry Primer, 1996.
• Harwood, Polar Rearrangements, Oxford Chemistry Primer, 1992.

Jerker Mårtensson