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I know that many prepositions can be followed by то, чтобы if we want to relate the preposition to a new sentence, rather than just a noun.

  • Вместо того, чтобы...
  • Настаивать на том, чтобы...
  • Отказаться от того, чтобы... etc.

However, these may be set expressions. Apparently the conjunction чтобы cannot be used with just every preposition.

Once I heard that кроме того, чтобы is incorrect, and must be replaced with кроме как.

Here's my attempt at numbering a few usages of то, что and то, чтобы.

Надеяться на то, что...

Вопреки тому, что...
Удивиться тому, что...

Жалеть о том, что...

Надо, чтобы...

  1. Maybe the correct conjunction must be memorized for each case?

  2. Still left an example with тем (instrumental).

The verb рисковать takes the instrumental case, thus we say рисковать жизнью.

But what if I want to risk a more elaborate sentence? Like "He risks losing his reputation".

Even though I could simplify and just say "Он рискует потерей своей репутации", if I wanted to connect рискует to another verb, could the sentence become "Он рискует тем, чтобы потерять свою репутацию"?

  1. Finally, if I want to say "on the brink of..." something other than a noun.

"On the brink of death" would be на грани смерти. But "on the brink of losing his job" wouldn't be "на грани того, чтобы быть уволенным"?

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  • Since чтобы includes the conditional mood particle бы, чтобы is used when what follows it hasn't happened yet, and it is seen as [un]desireble, [im]possible, proposed, suggested. – Yellow Sky Jul 12 '18 at 20:43
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  1. With рискует the subordinate clause is appended with the conjunction что and assumes future tense рискует тем, что потеряет, but another way of attaching a verb is to simply say рискует потерять

  2. This is correct but another, a more compact version, is again the simple на грани быть уволенным, still this only seem to work for the verb быть and maybe also стать.

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  • На грани увольнения would be even more compact. – AR. Jul 13 '18 at 2:56
  • indeed, but the OP looks specifically for the way to attach a verb – Баян Купи-ка Jul 13 '18 at 6:49
  • The complete version на грани того, чтобы быть уволенным sounds perfect to me while the 'compact' one does not. It is OK to use 'noun+infinitive' expressions like нежелание быть уволенным (мастер делать то-то, etc), but 'грань быть уволенным' sounds strange. Looks like the noun in such a construction should point at the person to be fired (нежелание is someone's wishing not) while на грани (рубеже, пороге) refers to the possibility of the action instead (грань, порог, рубеж увольнения - those are proper 'compact' expressions). – Alex_ander Jul 13 '18 at 12:39
  • он - на грани быть уволенным seems pretty palatable, i do agree that на грани увольнения is more idiomatic – Баян Купи-ка Jul 13 '18 at 14:25
  • Aside from nouns meaning personal abilities or qualities, the nouns paired with an infinitive usually somehow point at the cause of its action ("обусловливающие действие условия или обстоятельства"): books.google.ru/books/… (Грамматика русского языка в упражнениях и комментариях, О. Глазунова - 2017, c. 90) But the expression на грани is not about a condition causing some action: грань is a static thing, just a border between parts of an imaginary space. – Alex_ander Jul 15 '18 at 10:03

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