Investigation of Substituent Effects of 2-Substituted Silaethylenes

• Main Author: Snyder, Walter David
• Other Authors: Jones, Paul R.
• Format: Others
• Language: English
• Published: North Texas State University 1980
• Subjects: silicon-carbon double bonds; Substitution reactions.; Silaethylenes.; carbon substituents; silicon substituents
• Online Access: https://digital.library.unt.edu/ark:/67531/metadc504095/

This investigation is concerned with determining whether a carbon substituent or a silicon substituent on the carbon terminus of a silicon-carbon double bond has a more stabilizing effect. Two different 2-substituted silaethylenes were generated at the same time by pyrolyzing 1, 1-dimethyl-2-neopentyl-4- (dimethylalkoxysilyl) silacyclobutanes in a nitrogen flow system. The results of these pyrolyses, both neat and in the presence of a trapping reagent, show that the silaethylene with a silicon substituent on the carbon terminus was favored approximately two to one over the silaethylene with a carbon substituent. This datum, along with other observations and hypotheses discussed, leads to the suggestion that the silicon substituenton the carbon terminus of the silaethylene bond has a more stabilizing effect than the carbon substituent.