Good morning, Frank;
I agree with Jeff M. If you have the 100 mm f 2.5, use it. The teleconverter, whether it is for those up to 300 mm (the "S") or the one for those 200 mm and longer (the "L") (and, yes, there is a slight overlap between the two), will result in some loss of lens resolution and contrast. There are some factors in optical physics not even Leica and Hasselblad have been able to overcome. However, the 50 mm f 1.4 with the 300-S might have application as a 100 mm f 2.8 semi-soft-focus portrait lens combination.
While the 300-S and 300-L were designed for use with the MD lenses, they will couple to the MC lenses also. I have not tried an SR lens, but I cannot think of why it should not work.
Enjoy;
Ralph Javins