okay, one more for the road
did the random word thing, and here's the first hit in _Organic Synthesis_ with the word "overflow". ("untidy" gave nothing at all)
synthesis of 2,2-diethoxyethyl isocyanide! well, that's a thing I guess. it probably stinks to high heaven (organic isocyanides are famously stinky)
ah yeah they even warn you:
Caution: All the operations must be conducted in an efficient hood because the isocyanide has an obnoxious odor.
the reactions are pretty straightforward. aminoacetaldehyde diethyl acetal (or, 2,2-diethoxyethylamine, if you like) is turned into the formamide with propyl formate (why propyl formate? the reaction is carried out at reflux, suppose propyl formate boils at a high enough temperature to make the reaction work)
then the formamide is dehydrated to the isocyanide with the reagent you get from reacting carbon tetrachloride and triphenylphosphine. that's a trick a few uses (see the "Appel reaction")
