Chemoselectivity in the Reactions of Acetylketene and Acetimidoylketene: Confirmation of Theoretical Predictions

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7114-7120

  Birney, David M ^a   Xu, Xiaolian ^a   Ham, Sihyun ^a   Huang, Xiaomeng ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001294103     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971083d     Document Type: Article

References (64)

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2. For reviews, see: (a) Wentrup, C.; Heilmayer, W.; Kollenz, G. Synthesis 1994, 1219-1248. (b) Tidwell, T. T. Ketenes; John Wiley & Sons: New York, 1995; pp 665.
3. See also: (c) Kappe, C. O.; Wong, M. W.; Wentrup, C. J. Org. Chem. 1995, 60, 1686-1695. (d) Zuhse, R. H.; Wong, M. W.; Wentrup, C. J. Phys. Chem. 1996, 100, 3917-3922. (e) Zawacki, F. J.; Crimmins, M. T. Tetrahedron Lett. 1996, 37, 6499-6502. (f) Allen, A. D.; Andaos, J.; Kresge, A. J.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1992, 114, 1878-1879.
4. See also: (c) Kappe, C. O.; Wong, M. W.; Wentrup, C. J. Org. Chem. 1995, 60, 1686-1695. (d) Zuhse, R. H.; Wong, M. W.; Wentrup, C. J. Phys. Chem. 1996, 100, 3917-3922. (e) Zawacki, F. J.; Crimmins, M. T. Tetrahedron Lett. 1996, 37, 6499-6502. (f) Allen, A. D.; Andaos, J.; Kresge, A. J.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1992, 114, 1878-1879.
5. See also: (c) Kappe, C. O.; Wong, M. W.; Wentrup, C. J. Org. Chem. 1995, 60, 1686-1695. (d) Zuhse, R. H.; Wong, M. W.; Wentrup, C. J. Phys. Chem. 1996, 100, 3917-3922. (e) Zawacki, F. J.; Crimmins, M. T. Tetrahedron Lett. 1996, 37, 6499-6502. (f) Allen, A. D.; Andaos, J.; Kresge, A. J.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1992, 114, 1878-1879.
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44. 24
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49. 12 Thus we expect that the ketene reached the cold trap.
50. We have recently compared the ab initio transition structures for the [3 + 2] cycloadditions of formaldehyde and acetone to nitrosoketene. Although bond formation at the carbon of acetone is less than that in formaldehyde, both are concerted reactions, and the barriers are similar. Ham, S.; Birney, D. M. Tetrahedron Lett. 1997, 38, 5925-5928.
51. 3a
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57. No great significance is necessarily attached to this rather strange result. It may reflect the limitations of single-point energy calculations for low barrier reactions.
58. 25
59. Inconsistent results were obtained with larger dead space, presumably due to selective vaporization of the more volatile of the traps.
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