Pericyclic Reactions and Organic Photochemistry

Overview

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PRE-REQUISITES: Basic course in organic chemistry, stereochemistry and reaction mechanisms

INTENDED AUDIENCE: Core for post-graduates, Post-graduate and upper-level undergraduate, Final Year BSc, MSc and PhD

INDUSTRIES APPLICABLE TO: Pharma and fine chemical industry R&D labs, National labs such as NCL, IICT etc

COURSE OUTLINE: Concerted organic reactions and organic photochemistry are important topics in any Chemistry postgraduate curriculum. Pericyclic reactions which come under concerted organic reactions are governed by Woodward-Hoffmann rules. This course will uncover all the major topics in pericyclic reactions and organic photochemistry.

Syllabus

Activation of chemical reactions. Thermal and photochemical methods.
MOs of polyene and their symmetry properties and methods of analyzing pericyclic reactions.
Introduction to electrocyclic reactions and Woodward Hoffmann rules.
Electrocyclic reactions – examples of 3, 4 and 5 membered ring systems (2e and 4e systems).
Electrocyclic reactions – examples of 6 and larger ring systems (6e and more).
Tutorial session 1.
Cycloaddtion reactions - Introduction and Woodward Hoffmann rules - [2+2] cycloadditions.
Cycloaddition reactions – ketene cycloadditions.
Cycloaddition reactions – Diels-Alder reaction - Woodward Hoffmann rule -.
Diels Alder reaction - synthetic applications.
Diels Alder reaction continued - Hetero diene and dienophile - Lewis acid mediated - asymmetric.
1,3-Dipolar cycloaddition reactions.
1,3-Dipolar cycloaddition reactions continued.
[4pi+4pi], [4pi+6pi] and higher order cycloaddition reactions.
Tutorial session 2 on cycloaddition reactions.
Pericyclic reactions – Sigmatropic rearrangements – Introduction and [1,3] migrations.
Pericyclic reactions – Sigmatropic rearrangements continued…[1,5] H and C migrations.
Pericyclic reactions – Sigmatropic rearrangements continued…oxy Cope and Claisen Rearrangement.
Pericyclic reactions – Sigmatropic rearrangements continued….
Pericyclic reactions – Sigmatropic rearrangements continued…[2,3] sigmatropic shifts.
Pericyclic reactions – Sigmatropic rearrangements continued…Wittig rearrangement and higher order.
Pericyclic reactions – Tutorial session 3 - Problems on sigmatropic reactions.
Pericyclic reactions – Chelotropic reactions - introduction, SO2 extrusion reactions.
(Chelotropic reactions 2).
THE ENE REACTION.
Tutorial session - 4.
Introduction to organic photochemistry.
Photochemistry of alkenes cis-trans isomerization.
Photochemistry of alkenes (continued).
Photochemistry of carbonyl compounds, Norrish type1 and 2 reactions.
Photochemistry of carbonyl compounds, enone and dienone photochemistry.
Photochemistry of Nitrogen compounds.
Photochemistry of aromatic compounds.
Photoinduced electron transfer reactions.