Propynal equivalents and diazopropyne: Synthesis of all mono-13C isotopomers

Helvetica Chimica Acta

Volumn 92, Issue 8, 2009, Pages 1626-1643

  Seburg, Randal A ^a,b   Hodges, Jonathan A ^a,c   McMahon, Robert J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b CIMA Labs Inc Minnesota   (United States)

^c Affinergy Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C SUBSTITUTION; DIAZO COMPOUNDS; ISOTOPOMERS; PROPYNALS; SPECTROSCOPIC INVESTIGATIONS;

ACETYLENE; ALDEHYDES; LABELS;

ISOTOPES;

ACETAL; ALDEHYDE; ALKYNE; AZO COMPOUND; CARBON 13; HYDRAZONE DERIVATIVE; HYDROCARBON; PROPYNAL; PROPYNAL TOSYLHYDRAZONE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HYDROLYSIS; INFRARED SPECTROSCOPY; ISOTOPE LABELING; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; SYNTHESIS;

EID: 69249215295     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200800446     Document Type: Article

References (61)

1. X. Gu, Y. Guo, F. Zhang, R. I. Kaiser, J. Phys. Chem. A 2007, 111, 2980.
2. F. Leonori, R. Petrucci, E. Segoloni, A. Bergeat, K. M. Hickson, N. Balucani, P. Casavecchia, J. Phys. Chem. A 2008, 112, 1363.
3. W. Boullart, K. Devriendt, R. Borms, J. Peeters, J. Phys. Chem. 1996, 100, 998.
4. C. A. Taatjes, S. J. Klippenstein, N. Hansen, J. A. Miller, T. A. Cool, J. Wang, M. E. Law, P. R. Westmoreland, Phys. Chem. Chem. Phys. 2005, 7, 806.
5. R. I. Kaiser, Chem. Rev. 2002, 102, 1309.
6. E. Herbst, Chem. Soc. Rev. 2001, 30, 168.
7. P. Thaddeus, M. C. McCarthy, M. J. Travers, C. A. Gottlieb, W. Chen, Faraday Discuss. 1998, 109, 121.
8. E. Hébrard, M. Dobrijevic, Y. Bé nilan, F. Raulin, J. Photochem. Photobiol., C 2007, 7, 211.
9. C. P. Casey, S. Kraft, D. R. Powell, J. Am. Chem. Soc. 2000, 122, 3771.
10. C. P. Casey, S. Kraft, D. R. Powell, J. Am. Chem. Soc. 2002, 124, 2584.
11. A. Padwa, D. J. Austin, Y. Gareau, J. M. Kassir, S. L. Xu, J. Am. Chem. Soc. 1993, 115, 2637.
12. E. C. Hansen, D. Lee, Acc. Chem. Res. 2006, 39, 509.
13. R. A. Seburg, J. T. DePinto, E. V. Patterson, R. J. McMahon, J. Am. Chem. Soc. 1995, 117, 835.
14. R. A. Seburg, R. J. McMahon, Angew. Chem., Int. Ed. 1995, 34, 2009.
15. R. A. Seburg, E. V. Patterson, J. F. Stanton, R. J. McMahon, J. Am. Chem. Soc. 1997, 119, 5847.
16. R. A. Seburg, E. V. Patterson, R. J. McMahon, J. Am. Chem. Soc. 2009, submitted.
17. W. H. Dawson, R. B. Dunlap, J. Labelled Compd. Radiopharm. 1979, 16, 335.
18. E. J. Corey, R. A. Ruden, Tetrahedron Lett. 1973, 14, 1495.
19. H. M. Schmidt, J. F. Arens, Recl. Trav. Chim. Pays-Bas 1967, 86, 1138.
20. C. L. Rand, D. E. Van Horn, M.W. Moore, E. Negishi, J. Org. Chem. 1981, 46, 4093.
21. C. Eaborn, A. R. Thompson, D. R. M. Walton, J. Chem. Soc. C 1967, 1364.
22. D. R. M. Walton, F. Waugh, J. Organomet. Chem. 1972, 37, 45.
23. G. M. Coppola, Synthesis 1984, 1021.
24. D. Seebach, Angew. Chem., Int. Ed. 1979, 18, 239.
25. D. Seebach, Synthesis 1969, 1, 17.
26. N. B. Desai, N. McKelvie, F. Ramirez, J. Am. Chem. Soc. 1962, 84, 1745.
27. E. J. Corey, P. L. Fuchs, Tetrahedron Lett. 1972, 13, 3769.
28. D. Grandjean, P. Pale, J. Chuche, Tetrahedron Lett. 1994, 35, 3529.
29. A. J. Speziale, K.W. Ratts, J. Am. Chem. Soc. 1962, 84, 854.
30. M. C. McIntosh, S. M. Weinreb, J. Org. Chem. 1993, 58, 4823.
31. R. Hässig, D. Seebach, Helv. Chim. Acta 1983, 66, 2269.
32. H. Siegel, D. Seebach, J. Labelled Compd. Radiopharm. 1980, 17, 279.
33. E. V. Dehmlow, M. Lissel, Tetrahedron 1981, 37, 1653.
34. J. C. Sauer, in 'Organic Syntheses', Ed. N. Rabjohn, Wiley, New York, 1963, Coll. Vol.4, p. 813.
35. D. Makula, P. Lamy, Actual. Chim. 1983, 31.
36. T. J. de Boer, H. J. Backer, in 'Organic Syntheses', Ed. N. Rabjohn, John Wiley & Sons, New York, 1963, Coll. Vol.4, p. 250.
37. T. H. Black, Aldrichimica Acta 1983, 16, 3.
38. J. Otera, 'Esterification: Methods, Reactions, and Applications', Wiley-VCH, Weinheim, 2003.
39. T. Sammakia, 'Diazomethane', in 'e-EROS - Encyclopedia of Reagents for Organic Synthesis', Eds. L. A. Paquette, D. Crich, P. L. Fuchs, G. Molander, John Wiley & Sons, 2006, doi: 10.1002/047084289X.rd017.
40. S. Wierlacher, W. Sander, C. Marquardt, E. Kraka, D. Cremer, Chem. Phys. Lett. 1994, 222, 319.
41. W. Kirmse, A. Engelmann, J. Heese, Chem. Ber. 1973, 106, 3073.
42. C. Laurence, J. Guillemé, B. Kirschleger, J. Chem. Soc., Perkin Trans. 2 1981, 1341.
43. T.W. Greene, P. G. M.Wuts, 'Protective Groups in Organic Synthesis', 3rd edn., JohnWiley & Sons, New York, 1999.
44. G. Noronha, K. T. Nguyen, Tetrahedron Lett. 1999, 40, 4935.
45. T. R. Kelly, P. N. Kaul, J. Org. Chem. 1983, 48, 2775.
46. A. C. Gyorkos, J. K. Stille, L. S. Hegedus, J. Am. Chem. Soc. 1990, 112, 8465.
47. E. Winterfeldt, Synthesis 1975, 617.
48. S. A. Patwardhan, S. Dev, Synthesis 1974, 348.
49. W. Kirmse, A. Engelmann, Chem. Ber. 1973, 106, 3086.
50. K. Arai, H. Iwamura, M. Oki, Bull. Chem. Soc. Jpn. 1975, 48, 3319.
51. N. Miyaura, H. Suginome, A. Suzuki, Bull. Chem. Soc. Jpn. 1982, 55, 2221.
52. M. D'Auria, A. De Mico, F. D'Onofrio, G. Piancatelli, J. Org. Chem. 1987, 52, 5243.
53. G. Stork, K. Zhao, Tetrahedron Lett. 1989, 30, 287.
54. M. Dedieu, Y. L. Pascal, J. J. Basselier, P. Dizabo, J. Labelled Compd. Radiopharm. 1976, 12, 389.
55. G. V. Kroshtal, D. Dvorzhak, Z. Arnold, L. A. Yanovskaya, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1986, 35, 838.
56. H. Stetter, K. H. Mohrmann, Synthesis 1981, 129.
57. F. H. Sangsari, F. Chastrette, M. Chastrette, Synth. Commun. 1988, 18, 1343.
58. A. Stambouli, F. Chastrette, R. Amouroux, M. Chastrette, G. Mattioda, A. Blanc, Tetrahedron Lett. 1986, 27, 4149.
59. D. Seebach, B.W. Erickson, G. Singh, J. Org. Chem. 1966, 31, 4303.
60. L. Brandsma, 'Preparative Acetylenic Chemistry', Elsevier, Amsterdam, 1971, pp. 118 - 119.
61. F. Barbot, P. Miginiac, Bull. Soc. Chim. Fr. II 1983, 41.