D. Seyferth, Horst Menzel, A. W. Dow
Nov 1, 1972
Citations
1
Influential Citations
66
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract Trimethylsilyldiazomethane was prepared by the action of aqueous KOH on nitroso-N-(trimethylsilylmethyl)urea. The spectroscopic properties of this stable, greenish-yellow liquid which can be isolated by gas chromatography are discussed. Its reaction with acetic acid gives the expected CH3CO2CH2SiMe3 in addition to SiC cleavage products, CH3CO2CH3 and CH3CO2SiMe3. Products of the 1,3-dipolar addition of Me3SiCHN2 to activated olefins were not very stable, and only the adduct with acrylonitrile was isolated as a pure material Trimethylsilyldiazomethane undergoes Me3SiCH transfer to olefins, giving trimethylsilyl-substituted cyclopropanes, in the presence of CuCI in benzene, but other products are formed as well. Thus such a reaction with cyciohexenegave anti-7-trimethylsilylnorcarane (65%), syn-7-trimethylsilylnorcarane (7%), cis- and trans-l,2-bis(trimethylsilyl)ethylene (9% and 13%, respectively), and an unidentified Me3SiCH trimer (2.3%).