Answer? In 2004 Glennon, et al investigated the effects of B-oxygenated PEA/PPA's and used Hexamine on the bromoketone (thank Nicodem for pointing that out - I'd read it, but not SEEN it). Yeah, you are right - although IIRC the Delepine reaction is only when it is done with a benzyl
ketone halide isn't it? With subsequent hydrolysis to the benzaldehyde? This is kind of in the middle of Gabriel & Delepine, they are very similar mechanically - Delepine doesn't own all reactions of aliphatic halides with HMTA because He has a named reaction with the Benzyl ones & HMTA (
here). Yes, he only does so with the phenacyl bromide, the others (the propiophenones) he avoids by FC Acylation of the 2,5-dimethoxy-bromobenzene with N-Trifluoroacetyl-alaninoyl chloride. That is a reaction I'm looking at - quite frankly, if the fucking write-ups can agree about the products of citric acid + Cl[/sub]2[/sub](aq) (pH <3 favors the penta- and hexachloroacetone while anything nearing pH=7 gives predominantly CHCl
3), then the production of N-trichloroacetyl-alanine would be easy enough (from the hexachloroacetone).
I'm working with a couple of people over @WD on working out a synthesis of oxalyl chloride using only chlorine, sunlight, ethylene glycol and trichloroacetic acid, so if we solve the TCA problem, we may well have solved that one too.