Qing (Catherine) Ye made this carbene in collaboration with Phil Shevlin at Aubrun. Phil has shown that carbon atoms react in the gas phase with naphthalene to give the two possible naphthylcarbenes (only one is shown below). Those carbenes then fly to the walls of the reactor and add to alkenes. Sound improbable? Indeed it does, but Phil Shevlin has done lots of remarkable things, and we hoped to piggyback on this great reaction.

We simply replaced naphthalene with o-carborane in Phil's reactor. We knew from our own earlier work that carbenes - and thus very likely carbon atoms - reacted at the 9-position.

Why take this roundabout way to make the carbene? All the conventional ways fail, at least for us. We had to work around the problem. Why make this carbene at all? For the answer to that you'll have to read the paper, which will appear in Tetrahedron Letters in early 2002.

Here's a picture of Phil Shevlin and MJ in the water near Heron Island, Australia. He's the one near the shark.