It would make sense if it was on the stressed syllable in the foreign word, but that doesn’t seem to be the case. For example, メリークリスマス. You don’t put a stress on the second syllable of “merrý” in English. If anything, it sounds shorter because it’s unstressed.
Is there a rule?
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That’s a good question… I don’t know.
I have noticed in loanwords from classical Latin, the vowel extender always seems to correspond with the macron (e.g. Latin Dīāna -> Japanese ディーアーナ; Latin Aurōra -> Japanese アウローラ)
But I have no idea what the logic is behind English loans.
Yes. It sounds closer to “merry” with a long い sound.
Also, the chōonpu usually takes the place of an R after a vowel.
I guess it’s based on how they say the word. A kunyomi of English, if you will
Because they don’t care about the actual pronunciation. They transliterate the word just as they would say it.
There are definitely rules. I don’t know them, but after studying Japanese for a while, you’ll become able to intuitively transcribe English words the way a Japanese person would.
Yes, there are “rules”, or, more precisely, there are conventions on how to transcribe the sounds of each foreign language. In your example: it’s not about stress, but the vowel itself. In Japanese, traditionally both the FLEECE and happY vowels (see [Lexical sets]( https://en.wikipedia.org/wiki/Lexical_set#Standard_lexical_sets_for_English)) are transcribed with long /iː/ (イー etc.). I think this might have to do with [happY tensing](https://en.wikipedia.org/wiki/Phonological_history_of_English_close_front_vowels#Happy-tensing): in a lot of English dialects, the vowel in “happ**y**” is more similar in quality to the one in “fl**ee**ce” than to the one in “k**i**t”. So Japanese renders this distinction in quality (which doesn’t exist in Japanese) as a length distinction, transcribing KIT with short イ, and both FLEECE and happY with long イー; even though if you were to categorize the English vowels by length, then obviously FLEECE is longer and both KIT _and_ happY are shorter.
TL;DR The rule is that the sound of a “y” at the end of a word is transcribed as long イー.
EDIT: Here’s another article you might find interesting: [Transcription into Japanese](https://en.wikipedia.org/wiki/Transcription_into_Japanese).