Journal of the American Chemical Society p. 218 - 221 (1992)
Update date:2022-07-30
Topics:
Tamao, Kobei
Nakagawa, Yoshiki
Ito, Yoshihiko
X-ray structural analysis of a 1-aza-2-silacyclobutane derivative, trans-1-(tert-butyldimethylsilyl)-2,2,4-triphenyl-3-isopropyl-1-aza-2- silacyclobutane (1), has been carried out for the first time. The 1-aza-2-silacyclobutane skeleton is of small angle strain, being nonplanar in relation to the nearly planar nitrogen atom, and has normal bond lengths, aside from the considerably long C-N bond. 1-Aza-2-silacyclobutanes undergo thermal decomposition around 200 °C in toluene to form a silanimine species, R2S=NR, and an olefin. The formation of silanimine has been confirmed by quantitative formation of the dimer and a 1:1 adduct with Me3SiOEt in the copyrolysis. The 3,4-trans and -cis isomers form trans and cis olefins, respectively. The decomposition rates obey the first-order rate law and decrease in the order 3,4-trans > 3,4-cis > 3,3,4-trisubstituted derivatives. The results are analyzed by the concerted [2s + 2a] cycloreversion mechanisms.
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