We have used Masamune-Roush conditions in Horner Wadsworth Emmons reactions with good results on a number of occasions. Last week we had a rare failure using 5-nitrofuraldehyde and diethyl methylsulfonylmethylphosphonate, with DBU as the base. So far the only product that I have identified by NMR is the phosphonate starting material. There may be some aldehyde remaining. TLC with UV detection showed many spots, some of which faded with time.
Does this furan have a propensity to react in other ways? I am told it may do single electron chemistry, but I don't have a reference for this. If we substituted the corresponding thiophene for this furan, are we likely to do any better? Thanks for any ideas.