Allylic rearrangement of 3,3,3-trichloro-1-propenyl ketones

Takeda, Akira; Tsuboi, Sadao

doi:10.1021/jo00833a046

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Cited by 8 publications

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Allylic Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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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 S N 1′ or S N 2′ reaction. This reaction has been found to be promoted by light, enzymes, solvents, acid, (especially the Lewis acids such as Eu(fod) PBr and NiCl 2 ) and transition metal catalysts (including tungsten, rhodium, cobalt and palladium). The allylic rearrangement has been extensively used to synthesize a variety of organic molecules.

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