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= −0.5. This suggests the electrophilic attack of carbon monoxide at a nitrogen anion complexed to cobalt in the transition state. Force field calculations show that octahedral 
doi:10.1016/S0040-4039(00)83963-5 
Copyright © 1986 Published by Elsevier Science Ltd. All rights reserved.
Andreas Spaltenstein, Philip A. Carpino and Paul B. Hopkins
Department of Chemistry, University of Washington, Seattle, WA 98195 U.S.A.
Received 10 September 1985.
Abstract
Treatment of a variety of aliphatic or aromatic primary amines with an N-chlorosuccinimideactivated allylic setenide affords in modest to good yield the corresponding allylically rearranged secondary amines. Examples are reported which define the scope and limitations of this process.
References
a). Undergraduate Research Associate: b) Searle Scholar, 1984-1987.
R.G. Shea, J.N. Fitzner, J.E. Fankhauser and P.B. Hopkins J. Org. Chem. 49 (1984), p. 3647. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (7)
J.N. Fitzner, R.G. Shea, J.E Fankhauser and P.B. Hopkins J. Org. Chem. 50 (1985), p. 419.
J.N. Fitzner, D.V. Pratt and P.B. Hopkins Tetrahedron Lett. 26 (1985), p. 1959. Abstract | 
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| View Record in Scopus | Cited By in Scopus (6)
Detty, M.R. J. Org. Chem. 2980. 45. 274.
T. Hori and K.B. Sharpless J. Org. Chem. 44 (1979), p. 4208. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (21)
J.P. Marino and R.D. Larsen J. Am. Chem. Soc. 103 (1981), p. 4642. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (19)
K. Takeki, M. Yasumura and K. Negoro J. Org. Chem. 48 (1983), p. 54.
All of the allylic selenides utilized herein were prepared by the displacement of allylic mesylates or halides with sodium phenyl selenide. See D.J. Clive Tetrahedron 34 (1978), p. 1049. Abstract | PDF (5098 K)
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K.B. Sharpless and R.F. Lauer J. Am. Chem. Soc. 94 (1972), p. 7154. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (81)
The reported yields represent chromatographically homogeneous substances of greater than 95% purity. All products were characterized by 1H NMR 500 or 80 MHz. IR. and low resolution MS. Selected compounds were analyzed by high resolution MS or C, H, N combustion analysis. 1H NMR data (500 MHz. CDCl,) for selected secondary amine products follows [entry: chemical shift (δ), integral (H′s). multiplicity-(s,d,t,q,m). J(Hz)]: 1: 1.28, 3. t: 1.77. 3. s: 2.10. 1. bs: 3.22, 2. s: 3.40. 2 , s: 4.19, 2. q: 4.87. 2, s: 3: 1.8. 1. bs: 3.74. 1. s: 3.75. 1, s: 4.23. 1. d. 7: 5.12. 1, d. 10; 5.21. 1, d. 18: 5.97, 1, ddd. 7, 10. 18; 7.2–7.4. 10, m: 5: 4.8. 1, bs: 5.05, 1. d. 7: 5.28, 1. d. 19: 5.32, 1, d, 10; 6.05, 1, ddd, 7. 10. 19: 6.55. 2, d, 9: 7.35, 5. m: 8.07. 2. d, 9: 14a: 1.18, 3, t: 2.97, 2, m: 3.49, 1, t; 3.72, 3, s: 3.83. 1. d, 7: 4.12. 2, dq: 5.04, 2. s: 5.24, 1. d. 8: 5.28. 1. d, 12: 5.77, 1, ddd. 7. 8, 12: 6.89, 2, d. 9: 7.12. 2, d. 9: 7.2-7.5, 5. m: 1Ab: 1.16, 3, t: 2.92. 2, m: 3.50. 1. t: 3.68, 3. s; 3.86, 1, d, 7: 4.10. 2. dq: 5.04. 2. s: 5.22. 1. d, 7: 5.26. 1, d. 11: 5.77, 1, ddd. 7.7,11: 6.89. 2, d, 8: 7.11, 2. d, 8: 7.2-7.5, 5. m.
A major by-product in the case of aniline (entry 7) appears (500 MHz 1H NMR, MS evidence) to bear X = phenylseleno in the secondary amine product, presumably resulting from electrophic aromatic substitution on the aniline ring.
We thank the Dreyfus Foundation, the donors of the Petroleum Research Fund. administered by the American Chemical Society. Research Corporation, and Scripps Immunology Clinic for financial support.
