Aston-Greenburg rearrangement

What is Aston-Greenburg rearrangement?

The Aston-Greenberg rearrangement was initially discovered by Aston and Greenberg in 1940. This chemical transformation involves the conversion of an α-haloketone into an ester through the migration of one of the alkyl or aryl groups in the ketone to the α-position of another moiety when treated with alkali alkoxide, such as NaOEt or NaOMe.

Aston-Greenburg rearrangement
Aston-Greenburg rearrangement

X = F, Cl, Br, I

The Aston-Greenberg rearrangement is commonly employed to produce the esters of tertiary α-carbon in various chemical applications.

References

alpha-Bromo Secondary Alkyl Ketones. I. Reaction with Sodium Alcoholates. A New Synthesis of Tertiary Acids by Rearrangement1,2
J. G. Aston and R. B. Greenburg
Journal of the American Chemical Society 1940 62 (10), 2590-2595
DOI: 10.1021/ja01867a003

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