Journal of Organic Chemistry p. 3850 - 3856 (1993)
Update date:2022-08-05
Topics:
Denmark, Scott E.
Marcin, Lawrence R.
A general and expeditious route for the preparation of functionalized 2,2-disubstituted 1-nitroalkenes has been developed.Conjugate 1,4-addition of complex zinc cuprates (RCu(CN)ZnI) to easily obtained (E)-1-nitroalkenes, followed by trapping with phenylselenenyl bromide and subsequent oxidative elimination, afforded the corresponding 2,2-disubstituted 1-nitroalkenes in good yields. 2-Alkyl-2-aryl- and 2,2-dialkyl nitroalkenes 4b-g were prepared in 76-88percent yield and obtained as E/Z isomeric mixtures, slightly favoring the Z isomer (ca. 1.0:1.5, E/Z).
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