Azomethine Ylide Precursors: A Simple Route to N-(Trimethylsilylmethyl) Imines¹

References

• Issued as N. R. C. C. Publication No. 28375
   Google Scholar
• Stukwisch , C. G. 1973 . Synthesis , : 469 For reviews see:
   Google Scholar
• Kellogg , R. M. 1976 . Tetrahedron , 32 : 2165
   Web of Science ®Google Scholar
• Huisgen , R. 1980 . Angew. Chem., Int. Ed. Eng. , 19 : 947
   Google Scholar
• Lown , W. J. 1984 . 1,3-Dipolar Cycloaddition Chemistry , Edited by: Padwa , A. Vol. 1 , 653 – 732 . New York : Wiley .
   Google Scholar
• Dehnel , A. , Griller , D. and Kanabus-Kaminska , J. M. in press . J. Org. Chem. ,
   Google Scholar
• Dehnel , A. , Kanabus-Kaminska , J. M. and Lavielle , G. in press . Can. J. Chem. ,
   Google Scholar
• Vedejs , E. , Larsen , S. and West , F. G. 1985 . J. Org. Chem. , 15 : 2170 For natural product syntheses see:
   Google Scholar
• Smith , R. and Livinghouse , T. 1983 . J. Org. Chem. , 48 : 1554
   Google Scholar
• Terao , Y. , Imai , N. , Achiwa , K. and Sekiya , M. 1982 . Chem. Pharm. Bull. , 30 : 3167
   Google Scholar
• Tsuge , O. , Kanemasa , S. , Yamada , T. and Matsuda , K. 1985 . Heterocycles , 23 : 2489 For examples see:
   Google Scholar
• Achiwa , K. , Imai , N. , Inaoka , T. and Sekiya , M. 1984 . Chem. Pharm. Bull. , 22 : 2878
   Google Scholar
• Smith , R. and Livinghouse , T. 1985 . Tetrahedron , 11 : 3559
   Google Scholar
• Vedejs , E. and Martinez , G. R. 1980 . J. Am. Chem. Soc. , 102 : 7993 Inter alia:
   Google Scholar
• Padwa , A. , Haffman , G. and Tomas , M. 1983 . Tetrahedron Lett. , 24 : 4303
   Google Scholar
• Tsuge , O. , Kanemasa , S. and Matsuda , K. 1985 . Bull. Chem. Soc. Jpn. , 58 : 1570
   Google Scholar
• Tsuge , O. , Kanemasa , S. and Matsuda , K. 1984 . J. Org. Chem. , 42 : 2688
   Google Scholar
• Originally available from Petrarch Systems Inc. under catalogue No. T3636.5, this compound has been deleted from the company's most recent listing
   Google Scholar
• Noll , J. E. , Speier , J. L. and Daubert , B. F. 1951 . J. Am. Chem. Soc. , 72 : 3897 This material can also be prepared by hydrolysis of the iminophosphorane intermediate depicted in Scheme 1 (no experimental details or yield given: Tsuge, O., Kanemasa, S., Hatada, A. and Matsuda, K., Bull. Chem. Soc. Jpn., 1986, 52, 2537), but it must then be separated from triphenylphosphine oxide
   Google Scholar
• Tsuge , O. , Kanemasa , S. and Matsuda , K. 1983 . Chem. Lett. , 1131 For a large scale preparation of this material using 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) as solvent in place of the highly toxic and carcinogenic hexamethylphosphoramide (HMPA), see: Anderson, W. K. and Milowsky, A. S., J. Med. Chem., 1986, 29, 2241
   Google Scholar