Tetrahedron p. 4223 - 4234 (1986)
Update date:2022-07-29
Topics: Synthesis Experimental
Baldwin, Jack E.
Adlington, Robert M.
Bottaro, Jeffrey C.
Kolhe, Jayant N.
Perry, Matthew W. D.
Jain, Ashok U.
The lithium salts of aldehyde t-butylhydrazones react with electrophiles (aldehydes, ketones, alkyl halides, crotonates) to form C-trapped t-butylazo-compounds; tautomerisation and hydrolysis gave α-hydroxy ketones, ketones, and γ-keto esters in good yield, thereby providing a convenient new acyl-anion equivalent.Reaction of these lithium salts with aldehydes and ketones, followed by elimination provided a new route to azo alkenes.
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