The Reaction of 2,2-Difluorovinyl Ketones with Amines: A Facile Method for Preparation of α-Oxoketenimines and Acetoacetylation of Amines

Synlett

Volumn 1996, Issue 3, 1996, Pages 243-245

  Ichikawa, Junji ^a   Yokota, Naoyuki ^a   Kobayashi, Masakuni ^a   Amano, Kazuhiro ^a   Minami, Toni ^a  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009606157     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5393     Document Type: Article

References (28)

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2. Clarke, D.; Mares, R. W.; McNab, H. J. Chem. Soc., Chem. Commun. 1993, 1026. Kappe, C. O.; Kollenz, G.; Leung-Toung, R.; Wentrup, C. J. Chem. Soc., Chem. Commun. 1992, 487. Kappe, C. O.; Kollenz, G.; Netsch, K. -P.; Leung-Toung, R.; Wentrup, C. J. Chem. Soc., Chem. Commun. 1992, 488. Cheikh, A. B.; Chuche, J.; Manisse, N.; Pommelet, J. C.; Netsch, K. -P.; Lorencak, P.; Wentrup, C. J. Org. Chem. 1991, 56, 970.
3. Clarke, D.; Mares, R. W.; McNab, H. J. Chem. Soc., Chem. Commun. 1993, 1026. Kappe, C. O.; Kollenz, G.; Leung-Toung, R.; Wentrup, C. J. Chem. Soc., Chem. Commun. 1992, 487. Kappe, C. O.; Kollenz, G.; Netsch, K. -P.; Leung-Toung, R.; Wentrup, C. J. Chem. Soc., Chem. Commun. 1992, 488. Cheikh, A. B.; Chuche, J.; Manisse, N.; Pommelet, J. C.; Netsch, K. -P.; Lorencak, P.; Wentrup, C. J. Org. Chem. 1991, 56, 970.
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14. For the preparation of β,β-difluroacrylates, see also: Bumgardner, C. L.; Burgess, J. P.; Everett, T. S.; Purrington, S. T. J. Fluorine Chem., 1992, 56, 189 and references cited therein.
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17. Among the examined amines, tert-butylamine is an exception in terms of an employed amount because of its lower nucleophilicity and the lower reactivity of the corresponding α-oxoketenimine, as shown in Table 1, Entries 3 and 5.
18. 23NO: C, 79.33; H, 9.01. Found: C, 79.10; H, 8.80.
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20. Acid is not necessarily needed for the hydrolysis, of which conditions depend on the employed amine.
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23. Wang, W. -B.; Roskamp, E. J. J. Org. Chem. 1992, 57, 6101. Witzeman, J. S.; Nottingham, W. D. J. Org. Chem. 1991, 56, 1713. Cossy, J.; Thellend, A. Synthesis, 1989, 753.
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27. Pak, C. S.; Yang, H. C.; Choi, E. B. Synthesis, 1992, 1213.
28. In addition, acetoacetylation of alcohols is also successfully accomplished in a similar manner. The reaction of 2 with the corresponding lithium alcoholates proceeded at 0 °C to room temperature and subsequent hydrolysis with aqueous HCl afforded the β-oxoesters in good yields. See also Ref. 13.