Lecture 31 Cope and Claisen Rearrangements

Lecture 31 Cope and Claisen Rearrangements - O H 1 NaOH Br...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
O H O Claisen Rearrangement 1. NaOH 2. B OH 200 ° * * Br 13 C = * Pericyclic C Reaction O H * Cyclic flow of electrons keto intermediate “not stable” Concerted not stable or A A S LUMO A HOMO LUMO A HOMO S S S S Diels Alder Diels Alder 4 π + 2 π Pericyclic Reaction 3 π + 3 π A B Cope Rearrangement Diels Alder Pericyclic Reaction Cope Pericyclic Reaction O O Claisen Pericyclic Reaction H H O O O O O O O +CO 2 How do you recognize a Cope Reaction? 1 2 3 4 5 redraw Cope heat Number the bonds Assess relative Is it a 1-5 diene? stability 2 5 1 4 3 redraw Cope redraw A B C D E
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
The following compound undergoes a rearrangement. N Cope redraw Predict the product. A B C N N N D E F N N N The following compound undergoes a rearrangement. N N N Cope redraw Predict the product. A B C N N N D E F N N N The following compound undergoes a rearrangement. Cope ** Predict the product. A B C D E Bullvalene Cope J.Chem.Ed Link Bullvalene 1 4 2 3 This molecule is confused.
Background image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 10/18/2010 for the course CHE 326 taught by Professor Fowler during the Fall '08 term at SUNY Stony Brook.

Page1 / 4

Lecture 31 Cope and Claisen Rearrangements - O H 1 NaOH Br...

This preview shows document pages 1 - 3. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online