Theoretical study of a termolecular mechanism for the reaction of (Trimethylsilyl)thiazole with carbonyl compounds

Yun Dong Wu, Jeehiun K. Lee, K. N. Houk, Alessandro Dondoni

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The mechanism of the addition of 2-silylthiazole to formaldehyde has been studied by ab initio calculations at the MP2/6-31+G*//6-31G* level. The reaction is predicted to occur by the concerted formation of an N-[(silyloxy)methyl]thiazolium-2-ylide intermediate followed by nucleophilic addition of the intermediate to another formaldehyde molecule. Loss of the first formaldehyde gives the addition product. An alternative mechanism involving 1,2-migration of the ylide to form 2-[(silyloxy)-methyl]thiazole is prevented because of the high activation energy of the 1,2-shift. A third mechanistic alternative involving the formation of an N-silylthiazolium-2-ylide through 1,2-silyl migration is also discounted due to a high activation energy.

Original languageEnglish (US)
Pages (from-to)1922-1926
Number of pages5
JournalJournal of Organic Chemistry
Issue number6
StatePublished - Mar 22 1996
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry


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