SUBJECT

Theoretical Organic Chemistry

lecture

Master

Faculty of Science

Chemistry MSc

2

Semester 2/4

Spring semester

Classification and rationalization of the pericyclic reactions on the basis of qualitative molecular orbital theory. Electrocyclizations with participation of 2, 4, and 6 electrons, the rule of conservation of symmetry. Possibilities for 2+2 cycloadditions. Reaction of carbenes with olefins. Radical 2+2 cycloadditions. Regioselectivity and electron demand in Diels-Alder reactions. Intramolecular Diels-Alder reactions. Rationalizations and practical use of sigmatropic rearrangements. Stereochemistry of [3+3] sigmatropic rearrangements. Higher sigmatropic rearrangements. The theory of photochemistry. General principles of ring closure reactions, synthetic applications. Baldwin-rules and their interpretation.

• F. A. Carey amd R. J. Sundberg: Advanced Organic Chemistry, Plenum Press, New York, 1990

• M. B. Smith, J. March: March’s Advanced Organic Chemistry, Wiley, New York, 2001

• I. Fleming: Frontier Orbitals and Organic Chemical Reactions. Wiley, London, 1976.