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Allylic Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr016

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Allylic Rearrangement. Comprehensive Organic Name Reactions and Reagents. 16:68–73.

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

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Abstract

In allylic rearrangement, and occasionally referred to as the allylic isomerization, allylic transposition, and allylic 1,3-rearrangement, migration of a carboncarbon double bond within a three-carbon system (i.e., allylic), often occurring on the nucelophilic substitution of allylic systems in which the nucleophile adds to the carbon-carbon double bond along with the cleavage of the allylic leaving group. The allylic rearrangement is also known as the SN1′ or SN2′ reaction. This reaction has been found to be promoted by light, enzymes, solvents, acid, (especially the Lewis acids such as Eu(fod) PBr and NiCl2) and transition metal catalysts (including tungsten, rhodium, cobalt and palladium). The allylic rearrangement has been extensively used to synthesize a variety of organic molecules.

Keywords:

  • SN1′ or SN2′ reaction;
  • Lewis acids;
  • electrophilic substitution;
  • super-conjugation

Featured Compounds

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  1. 1 - 3
Compound 1
Molecular Weight:230.2576
Molecular Formula:C11H18O5
InChIKey:QMDJLQIIQVTIHW-FUGMZQJXSA-N
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Compound 2
Molecular Weight:533.33
Molecular Formula:C24H46O5Sn
InChIKey:CPWTYEPVORNDCY-ISPRSZQASA-N
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Compound 3
Molecular Weight:244.2842
Molecular Formula:C12H20O5
InChIKey:DSCDXIRLLLYRBI-VPJKUYQRSA-N
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