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A new synthesis of alpha,beta-unsaturated nitriles (13), esters (14), ketones (15), or sulfones (16) starting from alpha-bromonitroalkanes (1) or alpha-chloronitroalkanes (2) is presented.The reaction of 1 or 2 with ethyl alpha-alkylcyanoacetate (3), diethyl alpha-alkylmalonate (4), ethyl alpha-alkylacetoacetate (5), alpha-alkyl beta-diketones (6), or ethyl alpha-alkyl-alpha-sulfonylacetate (7) followed by elimination of ethoxycarbonyl and nitro groups or acetyl and nitro groups gives 13, 14, 15, and 16.As the carbon-carbon bond-forming step proceeds via a free radical chain process, the reaction is less sensitive to steric hindrance than usual ionic reactions like aldol condensations, and highly substituted olefins are readily prepared.
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Reference：
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem