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

Title:	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
Authors:	Chern, JH Wu, HJ 應用化學系 Department of Applied Chemistry
Issue Date:	28-May-1998
Abstract:	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.
URI:	http://dx.doi.org/10.1016/S0040-4020(98)00277-4 http://hdl.handle.net/11536/32612
ISSN:	0040-4020
DOI:	10.1016/S0040-4020(98)00277-4
Journal:	TETRAHEDRON
Volume:	54
Issue:	22
Begin Page:	5967
End Page:	5982
Appears in Collections:	Articles

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