I'm a bit confused by what I've heard about the 75-300mm L. One review said that it was great, maybe better than the old 100-400mm. But a friend of mine went to Africa recently and wanted a new telephoto for the trip. He bought/tried the 75-300mm L and said that it was absolutely terrible, so he got the 100-400mm instead.
Are you saying that the 75-300 cant be extended to a 400 or that IQ is lost if done?
Canon says it's not compatible with their teleconverters. You could probably use an off brand teleconverter, but I haven't heard of any that are of the same quality as the Canon ones (for Canon lenses). Also, there is the issue of AF. Most cameras need a lens with a maximum aperture of at least F5.6 for auto focus to work. When you mount a teleconverter, it reduces the (effective) maximum aperture. The 1.4X is about one stop, the 2X is about two stops. So if you used the 2X on the 75-300mm...at 300mm, your max aperture would only be F11....not enough for AF. It would also make it rather hard to get good shutter speeds.
Canon U.S.A. : Consumer & Home Office : Extender EF 1.4X III
"Note: This lens is only compatible with fixed focal length L-series lenses 135mm and over, as well as the EF 70-200/2.8L, EF 70-200/2.8L IS, EF 70-200/4L, and EF 100-400/4.5-5.6L."
Canon U.S.A. : Consumer & Home Office : Extender EF 2x III
"Note: This lens is only compatible with fixed focal length L-series lenses 135mm and over, as well as the EF 70-200/2.8L, EF 70-200/2.8L IS, EF 70-200/4L, and EF 100-400/4.5-5.6L. Additionally, please see the lens and/or camera body manual for full compatibility information with the Extender EF 2X III."