A nice preparation of nitroalkenes appeared in the latest JOC. The work was reported by Concellon, et al., JOC, 2007, 72, 5421-5423.
I like the two obvious aspects of this work- catalytic use of NaI and the use of SmI2 for functional group modification. The use of 0.15 eq of sodium iodide to catalyze the condensation is really clever. The yields are reported to range from 55 % to 96 %. A few yields are in the mid 50’s range yet no mention is made of dimerization of the bromonitromethane, so I can assume that is not much of an issue.
The process uses an excess (2.5 eq) of SmI2 to afford overall 2 electron transfer to the substrate, resulting in loss of Br dot and oxygen, yielding an olefin with good stereospecificity. For the examples given, the E/Z ratios were all 98/2.
There are some downsides to the chemistry, I’ll admit. Plant management may not be keen on nitromethane derivatives. I know that nitromethane has been shown to be shock sensitive in the BOM impact test (personal communication). Depending on their threshold for these things, the plant safety patrol boys may have misgivings.
The economic merit of scaling up a process that uses SmI2 depends entirely on the value proposition, which can be readily calculated. Rare earths are reportedly of low toxicity, though I have not seen a primary reference for that assertion.
Most of the rare earth elements come from FSU or China. There is an accessible supply outside of the usual catalog companies, though you may have to do an electronic funds transfer in advance to some cramped office in Shanghai with a rep named Sylvia or Frank. Advanced payment and sketchy D&B data will make your accountants skittish. But it could be worth it for bulk material.
I’m increasingly aware of the interesting utility of more than a few of the rare earth elements. My work post-academia has taken me to many far off and exotic locations on the fabulous periodic table. The rare earth group is not the featureless corridor of nondescript trivalent cations that this organikker once believed. Fancy that.
Lamentations on Chemistry 
Cute reaction! Don’t think I’ve ever used anything in the f-block.
Bromonitromethane (neat) is explosive as well, and decomposes quite readily in solution at higher temperature… I once did a bunch of reactions involving a surprising debromination of arylbromides in refluxing nitromethane. We believed that the nitromethane aci form was grabbing the bromine to give BrCH2NO2. I tried like crazy to detect it until I read this:
2BrCH2NO2 —> 2HBr + H2O +N2 + 2CO
“… In fact the energy output of bromonitromethane is similar to TNT. Clearly this is not a pure compound that should be manufactured or used in unprotected facilities… Shipping drums of neat bromonitromethane would be equivalent to shipping high explosive bombs… The diluted (with hydrocarbons) material is used without isolation and thus without danger”
AA made some good points. The key observation is the evolution of noncondensable gas phase decomposition products like N2 and CO. As you suggest, the shock sensitivity of many explosive materials falls off dramatically when the material is diluted or wetted with some inert solvent. The Bromonitromethane is probably quite safe in diluted form. The producer of the bromide might even agree to dilute it for the user.