As an outsider to web development, @when would be a weird choice. If CSS wants to enable 3rd party tooling to take some of the syntax space, then it should declare some parts of the syntax never to be taken by core CSS (if it's not already done this way). Then this syntax clash would never be a problem between a 3rd party tool like sass and CSS.
In this case I think it's on sass to introduce the awkward workaround on the syntax clash.
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