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While watching the film Django Unchained I came across the phrase (I paraphrased it to make a direct word order).

I insist that you shake my hand.

But I'm curious if I can paraphrase it in the following ways:

I insist on you to shake my hand

I insist on your shaking my hand

Are they all correct and mean the same?

I've also heard people use objective instead of possessive in sentences with the same grammar as in the last one, but I'm not sure what is the difference.

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The first (that you) and the third (on your shaking) are grammatical. The middle one is not.

There is not a general principle involved: it is just the (unpredictable) properties of the verb insist. With certain other verbs, this construction is possible:

He prevailed on me to shake his hand.

(Prevail is unlikely to be used imperatively, because it implies overcoming unwillingness).

Neither of the other constructions is possible with prevail. Demand will accept only the first. (A to- infinitive clause is possible, but only without an agent being specified: He demanded to shake my hand.)

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