told him not to have done vs told him not to do it

[tom3m]

Could anybody clarify, what the difference in meaning between the two is? Are they both possible?

1) a) She warned him to be careful with her money.
b) She warned him to have been careful with her money.

2 a) He denied spending all the savings.
b) He denied having spent all the savings.

3 a) He complained about not being paid enough.
b) He complained about not having been paid enough.

4 a) She insisted on buying the tickets.
b) She insisted on having bought the tickets.

Since you always want the creator of a thread to try first, my explanation would be as follows:

The perfect conveys the idea of past. That is why I think that it expresses meaning similar to the so-called past perfect, i.e. He denied having spent all the savings. would mean 'He denied he had spent all the savings.' Providing this was right I would be still be unaware of the meaning of the latter sentence. I hope you can explain. Thanks a lot for your help.

 

[bhaisahab]

Could anybody clarify, what the difference in meaning between the two is? Are they both possible?

1) a) She warned him to be careful with her money.
b) She warned him to have been careful with her money.

2 a) He denied spending all the savings.
b) He denied having spent all the savings.

3 a) He complained about not being paid enough.
b) He complained about not having been paid enough.

4 a) She insisted on buying the tickets.
b) She insisted on having bought the tickets.

Since you always want the creator of a thread to try first, my explanation would be as follows:

The perfect conveys the idea of past. That is why I think that it expresses meaning similar to the so-called past perfect, i.e. He denied having spent all the savings. would mean 'He denied he had spent all the savings.' Providing this was right I would be still be unaware of the meaning of the latter sentence. I hope you can explain. Thanks a lot for your help.

1 b) is not possible.
4 b) is unlikely, there might be a context for it but I can't think of one.

 

[tom3m]

Thank you,
could you give me an explanation or a link to it?

 

[5jj]

Cb) She warned him to have been careful with her money.

You can warn people only (not) to do things in the future.

4 a) She insisted on buying the tickets.
b) She insisted on having bought the tickets.

4a) She said: I will buy the tickets. I insist!.
4b would mean that she insisted that she had bought the tickets. This sounds most unnatural. I found only one similar construction in COCA and none in BNC.