I am trying to understand the grammar of using ところ with に and で when using ところ to represent the time that actions have happened.

These are (ungrammatical) sentences I made up:

1) 私の犬は猫を見ていたところに急に走り出して追いかけた。

2) 昨日商店街で友達と遊んでいたところで友達の財布がスリに盗まれた。

I don't understand why these sound unnatural.

Compare these sentences with 1)




What is the difference between these sentences and my sentence that makes my one wrong?

Compare this sentence with 2) above, which uses a similar structure


Why does 買ったところで sound alright but 遊んでいた/遊んだところで sound strange with this grammar?

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