Chemical transformation of tetraacetal tetraoxa-cages to aza-cages and amido-cages mediated by iodotrimethylsilane and the combination of chlorotrimethylsilane and sodium iodide in nitriles

被引：13

作者：

Chern, JH ^{[1
]}

Wu, HJ ^{[1
]}

机构：

[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu, Taiwan

来源：

TETRAHEDRON | 1998年 / 54卷 / 22期

关键词：

D O I：

10.1016/S0040-4020(98)00277-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An one-pot conversion of tetraacetal tetraoxa-cages la-e to aza-cages 2a-e mediated by iodotrimethylsilane in alkyl nitriles at 25 degrees C via the ring expansion compound 9 as the reaction intermediate was discovered. A Ritter-type reaction was proposed for the mechanism of this conversion. On the other hand, reaction of tetraacetal tetraoxa-cages 1 with Me3SiCl and NaI in nitriles at 25 degrees C gave the amido-cages 12. Conjugated nitriles and Lewis acids, such as TiCl4 or BF3 . OEt2 were found to be ineffective for the conversion of era-cages to aza-cages. The structures of 2a and chemical transformation product 16 were proven by X-ray analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：5967 / 5982

页数：16

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