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@article{196794, author = {Pinkas, Jiří and Gaul, B. and Verkade, J. G.}, article_location = {Washington, D.C.}, article_number = {10}, keywords = {AZASILATRANES; NITROGEN}, language = {eng}, issn = {0002-7863}, journal = {Journal of the American Chemical Society}, title = {Group 13 Azatranes: Synthetic, Conformational, and Configurational Features.}, volume = {115}, year = {1993} }
TY - JOUR ID - 196794 AU - Pinkas, Jiří - Gaul, B. - Verkade, J. G. PY - 1993 TI - Group 13 Azatranes: Synthetic, Conformational, and Configurational Features. JF - Journal of the American Chemical Society VL - 115 IS - 10 SP - 3925 EP - 3925 PB - American Chemical Society SN - 00027863 KW - AZASILATRANES KW - NITROGEN N2 - The monomeric azatranes E(RNCH2CH2)3N 7 (E = B, R = Me), 8 (E = B, R = SiMe3), and 9 (E = Al, R = SiMe3) can be synthesized from E(NMe2)3 and (HRNCH2CH2)3N in low yields (6-37%). The azatrane 10 (E = Al, R = Me), formed in 64% yield by the analogous reaction, is a stable dimer featuring a four-membered MeNAlNMeAl ring in which the aluminum is five-coordinate as shown by H-1, C-13, and Al-27 NMR spectroscopic techniques (including two-dimensional ones). Compound 7 can be made in 30% yield by reacting 10 with B(OMe)3. Compound 8, in contrast to 7 and 9, exists as rigid enantiomers that interconvert slowly at room temperature on the NMR time scale owing to steric repulsion of the Me3Si groups. VT H-1 and B-11 NMR studies provide evidence for a concerted (rather than a stepwise) racemization mechanism (DELTAH(double dagger), 61 +/- 5 kJ.mol-1; DELTAS(double dagger), -36 +/- 13 J.mol-1 K-1) involving a symmetric (C3v) transition state that retains the transannular bond. ER -
PINKAS, Jiří, B. GAUL and J. G. VERKADE. Group 13 Azatranes: Synthetic, Conformational, and Configurational Features. \textit{Journal of the American Chemical Society}. Washington, D.C.: American Chemical Society, 1993, vol.~115, No~10, p.~3925-3931. ISSN~0002-7863.
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