Thanks starlight and Chemitant -- I agree about the pictures. It used to be kind of a pain in the ass to do, not to mention potentially dangerous, but now that The Hive has the upload feature so one can host their own pictures on the board it's so easy, not to mention worthwhile.
Although the 91% yield of 1-(2,5-dimethoxyphenyl)-2-nitropropene made me quite happy (and trust me, I almost gave up on that one at like the 30 day mark), I was most happy about the 1-(4-fluorophenyl)-2-nitropropene yield. I knew there had to be some way of getting better then 50% on that one..
Does anybody have any ideas why the 1-(2,5-dimethoxyphenyl)-2-nitropropene took so rediculously long to reach completion? I was thinking perhaps the ring methoxy's, by donating electron density to the ring and hence the carbonyl carbon via resonance, may decease the electrophilicity of the carbonyl carbon, making the initial attack by the nitroethane "enolate" less favorable. However, only the ortho methoxy can donate electron density in this manner. This idea fails then in that by the same rationale, piperonal should also be a poor candidate for the same reaction, but that compound went to completion in a mere 6 days. Perhaps it has to do with the elimination of water instead? Hope what I'm trying to say there makes sense, it's late and I'm fumbling words.
-SpicyBrown