Abstract
Silver phosphate-catalyzed silylene transfer from silacyclopropane 1 to 1-heteroatom-substituted alkynes resulted in alkoxy-, amino-, and alkylthiolate-substituted silacyclopropenes. Silver-catalyzed silylene transfer to 1-halo- and 1-sulfonyl-substituted alkynes led to insertion of silylene into the carbon-heteroatom bond. Attempts at copper-catalyzed insertion of carbonyl compounds into heteroatom-substituted silacyclopropenes led to rearrangement into silicon-substituted alkynes with a net silylene insertion into the carbon-heteroatom bond. Mechanistic studies were conducted utilizing crossover experiments. A mechanism involving transmetalation/elimination was supported by the observation of crossovers in double-labeling experiments for alkynyl sulfides, halides, and sulfones.
Original language | English (US) |
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Pages (from-to) | 6212-6219 |
Number of pages | 8 |
Journal | Organometallics |
Volume | 24 |
Issue number | 25 |
DOIs | |
State | Published - Dec 5 2005 |
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry