Electrocyclizations and Torquoselectivity
MacMillan Group Meeting
Andrew Capacci
4/24/13
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Understanding Pericyclic Reactions: Sigmatropic, Electrocyclic, and Cycloadditions, Study notes of Geometry
An in-depth exploration of pericyclic reactions, a type of organic reaction characterized by a cyclic rearrangement of bonds. three main classes of pericyclic reactions: sigmatropic, electrocyclic, and cycloaddition. It discusses the mechanisms, participants, and factors influencing the direction of these reactions, including torquoselectivity and substituent effects.
Typology: Study notes
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Electrocyclizations and Torquoselectivity
MacMillan Group Meeting Andrew Capacci 4/24/
Pericyclic Reactions
! Classes of pericyclic reactions
Sigmatropic Rearrangements Electrocyclic Rearrangements Cycloaddition Reactions !" = ± 2 !# = ± 2
Pericyclic Reactions
! Classes of pericyclic reactions
Sigmatropic Rearrangements Electrocyclic Rearrangements Cycloaddition Reactions !" = ± 2 !# = ± 2
! A concerted reaction wherein the transition state is
characterized as having a cyclic array of interacting orbitals.
What is a pericyclic reaction?
Pericyclic Reactions
! Classes of pericyclic reactions
Sigmatropic Rearrangements Electrocyclic Rearrangements Cycloaddition Reactions !" = ± 2 !# = ± 2
! A concerted reaction wherein the transition state is
characterized as having a cyclic array of interacting orbitals.
What is a pericyclic reaction?
Electrocyclic Reactions
! What other systems participate in electrocyclic reactions?
Electrocyclic Reactions
! What other systems participate in electrocyclic reactions?
Electrocyclic Reactions
! What other systems participate in electrocyclic reactions?
H H
Electrocyclic Reactions
! What other systems participate in electrocyclic reactions?
Electrocyclic Reactions
! What other systems participate in electrocyclic reactions?
R R R R R R R R R R R R
Electrocyclic Reactions
! What other systems participate in electrocyclic reactions?
disrotatory ring-closure disrotatory ring-closure R R R R R R R R R R R R R R R R
Electrocyclic Reactions
! What other systems participate in electrocyclic reactions?
conrotatory ring-closure conrotatory ring-closure R R R R R R R R R (^) R R R R R R R
Electrocyclic Reactions
! What other systems participate in electrocyclic reactions?
conrotatory ring-closure conrotatory ring-closure
! Higher order systems also undergo electrocyclic rearrangement in the same manner
R R R R R R R R R (^) R R R R R R R