Journal of Organic Chemistry p. 4040 - 4045 (1982)
Update date:2022-08-02
Topics:
Crumbie, Robyn L.
Nimitz, Jonathan S.
Mosher, Harry S.
The anion of 2-(2-nitroethyl)-1,3-dioxolane (4), prepared from the corresponding 2-bromo compound (3), undergoes condensation with acylimidazoles to give the 3-nitro-4-oxobutanal acetals (9), which can serve as valuable polyfunctional intermediates.Condensation with 1-(methoxyoxalyl)imidazole gives the tetrafunctionalized methyl 4-(1,3-dioxolan-2-yl)-3-nitro-2-oxobutanoate (13), which, however, decomposed on attempted deprotection of the ester function.The syntheses in excellent yields of simple α-nitro ketones and α-nitro esters from acylimidazoles and nitroethane and 2-nitropropane are also described.
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Doi:10.1139/v82-264
(1982)Doi:10.1016/0040-4020(82)85104-1
(1982)Doi:10.1021/jo0485233
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(1982)Doi:10.1021/jo01086a003
(1959)