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
Citation
Jh. Chern et Hj. Wu, 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, Tetrahedron, 54(22), 1998, pp. 5967-5982
Citations number
51
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
22
Year of publication
1998
Pages
5967 - 5982
Database
ISI
SICI code
0040-4020(1998)54:22<5967:CTOTTT>2.0.ZU;2-M
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 di scovered. A Ritter-type reaction was proposed for the mechanism of thi s conversion. On the other hand, reaction of tetraacetal tetraoxa-cage s 1 with Me3SiCl and NaI in nitriles at 25 degrees C gave the amido-ca ges 12. Conjugated nitriles and Lewis acids, such as TiCl4 or BF3 . OE t2 were found to be ineffective for the conversion of era-cages to aza -cages. The structures of 2a and chemical transformation product 16 we re proven by X-ray analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.