The reactions of tert-butyl-, sec-butyl-, and n-butyllithium with dimethylfluorovinylsilane include addition to the double bond to give both silene and silenoid intermediates, fluorine substitution, and a novel vinyl substitution. For the tert-butyllithium reaction, product stereochemistry and trapping experiments using both cyclopentadiene and methoxytrimethylsilane show that silenes are not formed in THF. In hexane about 67% of the 1,3-disilacyclobutanes obtained arise from silene dimerization while 33% are formed by silenoid coupling. In hexane the order of reactivity for addition, t-Bu > sec-Bu > n-Bu, is opposite that for fluorine substitution. The vinyl substitution is most significant with secondary alkyllithium reagents including the tert-butyllithium adduct to dimethylfluorovinylsilane and with sec-butyllithium itself. Evidence for the formation of vinyllithium or ethylene in the process could not be obtained.
| Identifer | oai:union.ndltd.org:unt.edu/info:ark/67531/metadc331711 |
| Date | 08 1900 |
| Creators | Cheng, Albert Home-Been |
| Contributors | Jones, Paul R., Thomas, Ruthanne D., Theriot, L. J., Conlin, Robert T., Brady, William Thomas |
| Publisher | North Texas State University |
| Source Sets | University of North Texas |
| Language | English |
| Detected Language | English |
| Type | Thesis or Dissertation |
| Format | v, 100 leaves : ill., Text |
| Rights | Public, Cheng, Albert Home-Been, Copyright, Copyright is held by the author, unless otherwise noted. All rights reserved. |
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