Synthesis and conformational analysis of 1,3-azasilinanes

被引：11

作者：

Shainyan, Bagrat A. ^{[2
]}

Kirpichenko, Svetlana V. ^{[2
]}

Kleinpeter, Erich ^{[1
]}

机构：

[1] Univ Potsdam, Inst Chem, D-14476 Potsdam, Golm, Germany

[2] Russian Acad Sci, Siberian Div, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia

来源：

TETRAHEDRON | 2012年 / 68卷 / 36期

基金：

俄罗斯基础研究基金会;

关键词：

1,3-Azasilinanes; Conformational analysis; Dynamic NMR spectroscopy; Quantum chemical calculations; Ring current effect; SPACE NMR SHIELDINGS; GAS ELECTRON-DIFFRACTION; LOW-TEMPERATURE NMR; CHEMICAL-SHIFTS; H-1-NMR SPECTRA; SILICON ANALOG; DYNAMIC NMR; VISUALIZATION; DERIVATIVES; C-13;

D O I：

10.1016/j.tet.2012.05.106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Isopropyl-3-methyl-3-phenyl-1,3-azasilinane 1 and 1-isopropyl-3,3-dimethyl-1,3-azasilinane 2 were synthesized and a detailed analysis of their NMR spectra, conformational equilibria and ring inversion processes is presented. Low temperature H-1/C-13 NMR spectroscopy, iteration of the H-1 NMR spectra and quantum chemical calculations showed slight predominance of the PheqMeax over the PhaxMeeq conformer of 1 at low temperature. The barrier for the chair to chair interconversion of both compounds was measured to be 8.25 kcal/mol. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：7494 / 7501

页数：8

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