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IANAL but my guess would be that whilst his TOC is technically copyright - it's an expression in fixed form after all - that won't be enough to stop someone else writing a book with the same structure.
He also seems to have fallen into the trap of thinking it's the idea that's valuable and not the execution. This strikes me as similar to the folks who think that if they wrote a book about a boy wizard going to wizarding school prior to 1997 that they can sue JK Rowling. Aside from the legal niceties there's an assumption that it was those elements (the idea) that accounts for the success and not the book itself as a whole.
Similarly if someone else writes a maritime history with the same structure as your friend it won't be that that makes or breaks its success, it'll be the quality of the writing, of the research, the interest in the subject matter itself.
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