Notes- The Stevens Rearrangement in the Benzomorphan Synthesis

The based‐promoted rearrangements of quaternary ammonium salts can be divided into two categories. In the Stevens rearrangement one‐alkyl group migrates from the quaternary nitrogen group to the alpha carbon atom of a second alkyl group. The Somelet‐Hayser rearrangement involves migration to the ortho position of a benzyl quaternary ammonium salt. When structurally feasible, both rearrangements may occur simultaneously although experimental conditions markedly affect the competing pathways.

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Stevens Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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The intramolecular thermal [1,2]‐electrophilic migration of an alkyl group from the heteroatom of an ylide to the adjacent carbanion center upon the treatment with a strong base, resulting in the formation of a neutral molecule such as sulfide or a tertiary amine is generally known as the Stevens rearrangement. It has been found that only under harsh conditions, does a phosphorus ylide undergo the Stevens rearrangement, and this particular rearrangement is also known as the phospha‐Stevens rearrangement. In general, the Stevens rearrangement occurs for the listed ylides bearing a rather acidic α‐proton but missing the β‐hydrogens, otherwise, the competitive Hofmann elimination may take place. The Stevens rearrangement is often competed with an auto‐oxidation/cleavage occurring at the low temperatures. It has been found that the configuration of the migratory group is moderately or highly retained after the migration to the adjacent carbon atom. This reaction has very broad application in organic synthesis.

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Notes- The Stevens Rearrangement in the Benzomorphan Synthesis

Cited by 16 publications

References 2 publications

Electronic Effects of para-Substituents on the Local Anesthetic Activity of 2-Diethylaminoethyl Benzoate and Related Compounds^1a,1b

Electronic Effects of para-Substituents on the Local Anesthetic Activity of 2-Diethylaminoethyl Benzoate and Related Compounds^1a,1b

The Base‐Promoted Rearrangements of Quaternary Ammonium Salts

Stevens Rearrangement

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Notes- The Stevens Rearrangement in the Benzomorphan Synthesis

Cited by 16 publications

References 2 publications

Electronic Effects of para-Substituents on the Local Anesthetic Activity of 2-Diethylaminoethyl Benzoate and Related Compounds1a,1b

Electronic Effects of para-Substituents on the Local Anesthetic Activity of 2-Diethylaminoethyl Benzoate and Related Compounds1a,1b

The Base‐Promoted Rearrangements of Quaternary Ammonium Salts

Stevens Rearrangement

Contact Info

Product

Resources

About

Electronic Effects of para-Substituents on the Local Anesthetic Activity of 2-Diethylaminoethyl Benzoate and Related Compounds^1a,1b

Electronic Effects of para-Substituents on the Local Anesthetic Activity of 2-Diethylaminoethyl Benzoate and Related Compounds^1a,1b