Tetrahedron p. 5967 - 5982 (1998)
Update date:2022-08-03
Topics:
Chern, Jyh-Haur
Wu, Hsien-Jen
An one-pot conversion of tetraacetal tetraoxa-cages 1a-e to aza-cages 2a-e mediated by iodotrimethylsilane in alkyl nitriles at 25 °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 °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 oxa-cages to aza-cages. The structures of 2a and chemical transformation product 16 were proven by X-ray analysis.
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