I want to understand the mechanism of desilylation of trimethylsilyl under fluoride conditions in methanol, because I can't find any useful info that makes me understand the mechanism that takes place.
Thank you in advance!
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https://chemistry.stackexchange.com/questions/47698/relative-basicity-of-fluorine-and-oxygen-in-silyl-ether-deprotection – Mithoron Mar 28 '20 at 18:59
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It does help a lot, but my case is a little bit different because a terminal alkyne is bonded to the silyl group instead of oxygen. Why would that bond be broken and not any other carbon bond? – Bram Mar 28 '20 at 19:34
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Think about the exceptional strength of an Si-F bond and the pKa of terminal alkynes vs other types, sp2 and sp3, C-H bonds. – user55119 Mar 28 '20 at 19:44