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Subject Expert
Assume the specialty group is also transactional in nature? Generally, the biggest barrier to retooling is your ability to stomach the pay/seniority cut that usually comes with starting over in a new practice area. The more different the practice area, the steeper that cut tends to be. But to answer your question, yes- I know of a senior lit associate who retooled into funds, a corporate associate who moved into L&E, etc.
Enthusiast
Have seen a few people at my shop doing that. Not super seniors (think 5-6th year) and retooled into corporate specialist groups as juniors. It can happen as long as you are generally liked and the group you are eyeing is busy.
Mentor
Yes, but they needed to go back down to second years.
I've seen senior associates retool into Fund Finance, but they need to take a lateral penalty (maybe come in as a fourth year?). Some firms allow you to earn class years back after a year or two if you're performing at a high level and they want to keep you.
Lit —> white collar
Mentor
I retooled from specialist to corporate. Took a two year class cut, which I thought was fair.