Journal of Organic Chemistry p. 1251 - 1263 (1988)
Update date:2022-07-30
Topics:
Denmark, Scott E.
Sternberg, Jeffrey A.
Lueoend, Rainer
A general method for the preparation of 3-substituted nitrocycloalkenes has been developed. 2-Nitrocycloalkanones are transformed into iether α-nitro N,N-dimethylhydrazones or α-nitro cyclohexylimines, which exist exclusively in the aci-nitro form.Double deprotonation of these materials with sec-BuLi produces higly reactive dianions which can by alkylated with methyl, allyl, n-butyl, isopropyl, or 4-hexenyl iodides in excelent yields.The alkylation occurred uniformly next to the hydrazone or imine function.The alkylated α-nitro hydrazones are converted to nitroalkenes by reduction with NaBH4 followed by elimination induced by heating (120 deg C) with acetic anhydride.The alkylated α-nitro imines undergo facile reduction-elimination with NaBH4/CeCl3 ar room temperature.The overal yield for 2-nitro ketone to nitroalkene transformation ranged from 35percent to 44percent for the hydrazone method and from 19percent to 39percent for the imine method.
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