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A 1-Aza-2-silacyclobut-3-ene and an Alkyne from [Li{Si(SiMe3 )3 }(thf)3 ] and the Isocyanide 2,6-Me2 C6 H3 NC
Peter B Hitchcock1, Michael F Lappert1, Marcus Layh1
1School of Chemistry, Physics and Environmental Science, University of Sussex, Brighton BN1 9QJ (UK), Fax: (+44) 1273-677196.
Abstract:
The novel zwitterionic heterocycle 1 was unexpectedly obtained from the reaction between [Li(SiR3 )(thf)3 ] and ArNC. Upon heating 1 underwent an interesting ring opening to give the alkyne 2. Hence the C≡C bond effectively arises from the C-C coupling of two ArNC moieties. R=SiMe3 , Ar=2,6-Me2 C6 H3 , tmeda=N,N,N',N'-tetramethylethylenediamine.
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The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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