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Teaching at the
University of Cologne


Lecture

Advanced
Organic
Chemistry

SoSe & WiSe 
Wed, 11:00 - 12:30
Org.Chem.
HS-III

Exams
where&when



Wellcome-
Information
SoSe20


Advanced Organic Chemistry
Reaction Mechanisms & Pericyclic Reactions -
Basic Principles & Synthetic Applications

Check-List-PERICYCLICS

-> Basic Principles

classes of pericyclic reactions 

history of the Diels-Alder-addition

MO vs VB

orbital-symmetry methods, orbital interactions

correlation diagrams

FMO-theory

Evans-,
Hückel-Möbius-, Dewar-Zimmerman-method

Aromaticity, Anti-Aromaticity

carben-additions, least & non-least-motion

DA-additions, endo-rule & explanation

sigmatropic cyclopentadiene-rearrangement

electrocyclic reaction of cyclopropyl-cations

thermal vs photochemical pericyclic reactions

photochemical DNA-damage

vitamin-D formation

-> Applications: cycloadditions

[2+2]-additions

pseudo-pericyclic-reactions

[2+2] in TM-catalyzed metatheses

peri-selectivity

cyclopropanations

DA-normal and -inverse

LA- and organo-catalyses

regio-selectivity

hetero-DA

retro-DA

cheletropic additions, extrusions

Schenck-ene-additions

Huisgen [3+2]-additions

click-reactions

Alder-ene-addition, menthol-synthesis

-> Applications: sigmatropic rearrangements

walk-rearrangements

Cope-rearrangement, bullvalene

Claisen-rearrangements

Fischer-indol synthesis

Wagner-Meerwein-shift

Wittig-rearrangements [1,2] vs [2,3]

-> Applications: electrocyclic-rearrangements

cyclopropyl-hydrolyses

Nazarov-cyclizations

Bergman- & Myers-Saito-cyclizations