No, this is not possible. In order for your device to be in debug mode/connect to the computer with the debug cable, it needs to be connected as a slave device. The OTG cable tells the tablet to go into host mode. So now your computer is telling your tablet to be a slave but through the enumeration with the OTG cable the tablet believes it needs to be the master, there's a quarrel and it appears the tablet wins and is the master and thus your computer does not acknowledge the tablet's existence.
If you need the debugging tools have you looked into ADB wireless debugging?
(Sorry I can't find the link right now but I've used it in the past and know it is somewhere on the developer.android.com site)
I couldn't find the link so I figured out how to do it again:
- Open the command prompt and navigate to your sdk/platform-tools/ folder.
adb tcpip 5555
adb connect <your device IP address>:5555
- At this point you unplug your device and type
- At times, such as unplugging/plugging into a USB device, the logcat will become disconnected, just redo steps 3 & 4.