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The aim of the course is to make students familiar with the concepts and applications in two important topics in advanced organic chemistry, namely concerted organic reactions and organic photochemistry.

Pericyclic reactions are concerted organic reactions and are governed by Woodward-Hoffmann rules. Different methods of analysis of pericyclic reactions to arrive at the Woodward-Hoffmann rules will be presented. Synthetic applications and mechanisms of various pericyclic reactions will be discussed. Similarly the concepts involved in understanding organic photochemical reactions, their mechansims and applications in organic synthesis will be presented.
This course will uncover all the major topics in pericyclic reactions and organic photochemistry.  In addition to lectures there will be tutorial sessions and assignments in this course.


WeekNo.

Topics

1.

General introduction to the course, activation of chemical reactions.  thermal and photochemical methods, molecular orbitals of conjugated polyenes and their symmetry properties, definition and classification of pericyclic reactions
methods of analyzing pericyclic reactions.

2.

Electrocyclic reactions – introduction, definition and classification, Woodward- Hoffmann rules for electrocyclic reactions, Stereochemical aspects and modes of electrocyclic reactions, analysis of electrocyclic reactions by various methods, examples of electrocyclic reactions.

3.

Electrocyclic (continued), Cycloaddition reactions, Woodward- Hoffmann rules for cycloaddition reactions, stereochemical aspects and modes of cycloaddition reactions, analysis of cycloaddition reactions by various methods

4.

Examples of thermal and photochemical [2p+2p] cycloaddition reactions
Synthesis of cage type compounds using [2p+2p] cycloaddition reactions
Diels-Alder reaction and its variants and their syntic utility

5.

1,3-Dipolar cycloaddition reactions, higher order cycloaddition reactions, sigmatropic rearrangements, Woodward Hoffmann rules for sigmatropic rearrangements

6.

 
Sigmatropic rearrangements – examples, Claisen and Cope rearrangements
[2,3]-sigmatropic rearrangements and higher order rearrangements
Chelotropic reactions - introduction, definition and classification, Ene reaction.

7.

Organic photochemistry – introduction, definitions, importance
Electronic excitation and spin configurations – Jabolanski diagram
Energy transfer and electron transfer processes – quenching of excited states
Photochemistry of carbonyl compounds

8.

Photochemistry of olefins, enones and dienones, photochemistry of aromatic molecules, molecular oxygen and organic photochemistry, supramolecular organic photochemistry.

Basic course in organic chemistry, stereochemistry and reaction mechanisms


1.S. Sankararaman, Pericyclic Reactions – A textbook. Wiley-VCH, 2005.

2.I. Fleming, Pericyclic Reactions, Oxford University Press, 1999.

3.N. J. Turro, V. Ramamurthy and J. C. Scaiano, Modern molecular photochemistry of organic compounds, University Science Books, 2010.



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