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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 7
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Original Articles

TiCl4 Induced N-Methyleneamine Equivalents. 21. First Synthesis of Anilinomethylazides

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Pages 969-975 | Received 01 Aug 1994, Published online: 23 Sep 2006

References

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  • 1,3,5-Triphenylhexahydro-1,3,5-triazine can be prepared by the conventional method with aniline and formaldehyde. This can be converted to N-(methoxymethyl)aniline under reflux with sodium methoxide in methanol except 2f.
  • Matsumura , Y. and Tomita , T. 1994 . Tetrahdron Lett. , 35 : 3737 Recently optically pure α-amino acids were prepared via α-azidoamine. see
  • Reaction Products 3a and 3c were readily decomposed with loss of azide during flash chromatography
  • As we reported early in ref. 1 we tentatively assume that the intermediate 5 is served as a N-methyleneamine equivalent excluding possibility of C-OCH3 bond cleavage before a nucleophile attacks. However, in case of α-alkoxycarbamate iminium ions i.e. conjugated N-acylium intermediate was generated as an equilibrium with the removal of alkoxy group in the presence of Lewis acids detected by 1H and 13C NMR spectra.15
  • Yamamoto , Y. , Nakada , T. and Nemoto , H. 1992 . J. Am. Chem. Soc. , 114 : 121

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