Transamination studies on N-(1-alkenylthio)phthalimides and related compounds. Synthesis of 1-alkenesulfenamides and 1-alkenesulfonamides

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4232-4239

  Refvik, Mitchell D ^a   Schwan, Adrian L ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000867222     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9522163     Document Type: Article

References (50)

1. Presented in part at the 16th International Symposium on the Organic Chemistry of Sulfur, Merseburg, Germany, July 10-15, 1994 and at the 78th Canadian Chemical Conference, Guelph, Ontario, May 28-June 1, 1995. Aspects of this project have been published in communication form. See: Schwan, A. L.; Refvik, M. D. J. Chem. Soc., Chem. Commun. 1995, 1949.
2. Presented in part at the 16th International Symposium on the Organic Chemistry of Sulfur, Merseburg, Germany, July 10-15, 1994 and at the 78th Canadian Chemical Conference, Guelph, Ontario, May 28-June 1, 1995. Aspects of this project have been published in communication form. See: Schwan, A. L.; Refvik, M. D. J. Chem. Soc., Chem. Commun. 1995, 1949.
3. Presented in part at the 16th International Symposium on the Organic Chemistry of Sulfur, Merseburg, Germany, July 10-15, 1994 and at the 78th Canadian Chemical Conference, Guelph, Ontario, May 28-June 1, 1995. Aspects of this project have been published in communication form. See: Schwan, A. L.; Refvik, M. D. J. Chem. Soc., Chem. Commun. 1995, 1949.
4. For reviews on the synthesis and reactions of sulfenamides see: (a) Craine, L.; Raban, M. Chem. Rev. 1989, 89, 689. (b) Capozzi, G.; Modena, G.; Pasquato, L. In The Chemistry of Sulfenic Acids and their Derivatives; Patai, S., Ed.; J. Wiley & Sons: New York, 1990; p 487.
5. For reviews on the synthesis and reactions of sulfenamides see: (a) Craine, L.; Raban, M. Chem. Rev. 1989, 89, 689. (b) Capozzi, G.; Modena, G.; Pasquato, L. In The Chemistry of Sulfenic Acids and their Derivatives; Patai, S., Ed.; J. Wiley & Sons: New York, 1990; p 487.
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34. Full practical details of the preparation of compounds 4 will presented elsewhere.
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37. 1H NMR and GC/MS revealed two isomeric N,N-bis(1-methylethyl)hexenesulfenamides in an expected ratio.
38. Compounds 6 are not particularly stable: they have a limited lifetime in the freezer and do not exhibit ideal chromatographic behavior. Loss of a benzoyl unit is one of their fates. For this reason, satisfactory elemental analysis could not be obtained. A referee has suggested that compounds 6 may not have the structures that we have assigned to them, but that they could possess C=O and C=N bonds rather than two C=O bonds. Indeed, based on our synthetic method, structures such as 1-alkenyl-SN-C(Ph)OC(O)Ph would also conform with the measured spectral data. The alternative isomers would also be expected to undergo chemistry consistent with our experimental observations.
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42. The solvent was DMSO. The sample decomposed rapidly above 185 °C.
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44. Other primary amines afforded mixtures containing a number of constituents whose identity changed thoughout workup. One component, isolated from a transamination attempt with n-hexylamine, was determined to be N,N′-dit(1-hexyl)phthalamide (19%).
45. 1H NMR spectra, but not in the spectrum of pure material.
46. 1H NMR spectra of the alkenesulfenamides 8 generated from transaminations of thiophthalimides 7. Only in the synthesis of sulfenamide 8a did we observe a ring-opening product of the type 13 (ca. 10%). Other experiments have shown that the ring-opened product would not survive the oxidation process.
47. Azide ion was the nucleophile, (tert-butylimino)phthalide was the substrate, see: Keung Au, T.; Baydar, A. E.; Boyd, G.V. J. Chem. Soc., Perkin Trans. 1 1981, 2884.
48. Expeditious proton removal from the quaternary nitrogen of 14 requires that the lone pair left behind is in conjugation with the carbonyl, see: Perrin, C. L. Acc. Chem. Res. 1989, 22, 268. It would seem logical that with more hydrogens on the nitrogen, the required conformation will be more achievable and the hydrogen transfer more rapid.
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