Let's not forget the 10 or so liters of THF and ether tragically lost to peroxide test strips.
Yeah, BBr3 is nasty. I wrap it into foil, put in plastic container and seal slits with parafilm - so that it can peacefully coexist with other bottles in a dessicator not covering everything with white dust.
BBr3 I loath to work with even more than Br2. Btw, what is BCl3 solution useful for - is it actually for ArOMe deprotection, or perhaps Friedel-Craft?Reminds me: A cleanup is EJC attic storeroom was memorable: First a giant safety officer named Littleboy knocked down a liter of TiCl4 and came down running the stairwell chased by a giant white plume, then an old over-pressurized bottle of iPrOCOCl blew up during the cleanup, and finally someone spilled hydrocinnamaldehyde in the freezer room, which made everyone participating in the cleanup smell like wearing a cheap loud aftershave
You know, I honestly don't know what that bottle of BCl3 was used for... I've been here 4 years and can't remember anyone telling me they used it - that doesn't mean someone didn't use it without telling me, of course ;)Off the top of my head, Noah Burns did do a BBr3 deprotection during the synthesis of haouamine, maybe it was screened then, but that was years ago, before my time.
As far as I remember, you can't take off ArOMe with BCl3, but you can remove ArOiPr. For the methoxy you need the more potent BBr3.It's a little protecting group trick that was recently used in Beaudry's total synthesis of Cavicularin (OL 2013 pp402-405).
We used it in the meroterpenoid paper. It was used to open up chromazonarol to zonarol/isozonarol.
Thank you for reminding me of that boronic-terpene paper; it was a particularly sweet way of making cyclized oligoprenoids.