Reactions of chlorosulfanyl derivatives of cyclobutanones with different nucleophiles

Helvetica Chimica Acta

Volumn 89, Issue 5, 2006, Pages 1042-1061

  Majchrzak, Agnieszka ^a   Mlostoń, Grzegorz ^b   Linden, Anthony ^a   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b UNIVERSITY OF LODZ   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; KETONES; PHENOLS; REACTION KINETICS; SULFUR COMPOUNDS; X RAY CRYSTALLOGRAPHY;

3-CHLORO-3-(CHLOROSULFANYL)-2,2,4,4-TETRAMETHYLCYCLOBUTAN- L-ONE; CYCLOBUTANONES; NUCLEOPHILES; SECONDARY AMINES;

SUBSTITUTION REACTIONS;

3 CHLORO 3 (CHLORODISULFANYL) 2,2,4,4 TETRAMETHYCYCLOBUTAN 1 ONE; 3 CHLORO 3 (CHLOROSULFANYL) 2,2,4,4 TETRAMETHYLCYCLOBUTAN 1 ONE; ALKANOL; AMINE; CHLORIDE; CYCLOBUTANONE DERIVATIVE; HYDROCHLORIC ACID; PHENOL DERIVATIVE; PHOSPHATE; SULFOXIDE; SULFUR; THIOL DERIVATIVE; THIOPHENOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; PRIORITY JOURNAL; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

EID: 33744952178     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200690082     Document Type: Article

References (76)

1. K. N. Koch, G. Mlostoń, A. Senning, Eur. J. Org. Chem. 1999, 83.
2. G. Mlostoń, A. Majchrzak, A. Senning, I. Sotoøfte, J. Org. Chem. 2002, 67, 5690.
3. K. Oka, S. Hara, Tetrahedron Lett. 1977, 8, 695.
4. C. D. Gabbutt, J. D. Hepworth, B. M. Heron, M. Kanjia, Tetrahedron 1994, 50, 827.
5. C. K. Johnson, ORTEPII', Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
6. I. El-Sayed, M. F. Abdel-Megeed, S. M. Yassin, A. Senning, Phosphorus, Sulfur, Silicon 1994, 86, 239.
7. L. N. Markovskii, V. M. Timoshenko, Yu. G. Shermolovich, Zh. Org. KMm. 1995, 31, 161;
8. Chem. Abstr. 1996, 124, 116274.
9. H. W. Roesky, A. May, M. Noltemeyer, J. Fluorine Chem. 1993, 62, 77.
10. G. Mlostoń, J. Romański, A. Linden, H. Heimgartner, Helv. Chim. Acta 1993, 76, 2147.
11. T. Saito, S. Motoki, J. Org. Chem. 1977, 42, 559.
12. S. Tamagaki, K. Sakaki, S. Oae, Bull. Chem. Soc. Jpn. 1974, 47, 3084.
13. T. Saito, S. Motoki, Chem. Lett. 1978, 591.
14. T. Saito, S. Motoki, J. Org. Chem. 1979, 44, 2493.
15. S. Holm, J. A. Boerma, N. H. Nilsson, A. Senning, Chem. Ber. 1976, 709, 1069.
16. T. Saito, M. Nakane, S. Motoki, Bull. Chem. Soc. Jpn. 1984, 57, 1429.
17. I. Crossland, Acta Chem. Scand. B 1977, 10, 890.
18. A. May, H. Roesky, D. Stalke, F. Pauer, G. M. Sheldrick, Chem. Ber. 1990, 123, 1475.
19. S. Tamagaki, K. Sakaki, S. Oae, Bull. Chem. Soc. Jpn. 1973, 46, 2608.
20. K. Oka, S. Hara, Tetrahedron Lett. 1977, 2939.
21. E. M. Burgess, H. R. Penton, J Am .Chem. Soc. 1973, 95, 279.
22. T. Saito, S. Motoki, J. Org. Chem. 1977, 42, 3922.
23. G. Mlostoń, J. Fabian, Pol. J. Chem. 1999, 75, 683.
24. R. Huisgen, G. Mlostoń, E. Langhals, Helv. Chim. Acta 2001, 84, 1805.
25. G. Mlostoń, J. Romański, A. Linden, H. Heimgartner, Pol. J. Chem. 1996, 70, 880.
26. G. Mlostoń, M. Celeda, H. W. Roesky, E. Parisini, J.-T. Ahlemann, Eur. J. Org. Chem. 1998, 459.
27. G. Mlostoń, J. Romański, H. Heimgartner, Pol. J. Chem. 1996, 70, 437.
28. G. Mlostoń, J. Romański, A. Linden, H. Heimgartner, Helv. Chim. Acta 1995, 78, 1067.
29. S. Braverman, D. Ytzhak, Tetrahedron 1990, 46, 2975.
30. M. E. Sitzmann, W. H. Gilligan, J. Org. Chem. 1983, 48, 3354.
31. E. O. John, J. M. Shreeve, J. Fluorine Chem. 1987, 36, 429.
32. W. G. Phillips, K. W. Ratts, J. Org. Chem. 1972, 37, 1526.
33. B. Zwanenburg, A. Wagenaar, L. Thijs, J. Strating, J. Chem. Soc., Perkin Trans, 1 1973, 73.
34. C. P. Raj, N. A. Dhas, M. Cherkinski, A. Gedanken, S. Braverman, Tetrahedron Lett. 1998, 39, 5413.
35. F. Scheufler, M. E. Maier, Eur. J. Org. Chem. 2000, 3945.
36. P. Bickart, F. W. Carson, J. Jacobus, E. G. Miller, K. Mislow, J Am. Chem. Soc. 1968, 90, 4869;
37. R. Tang, K. Mislow, J. Am. Chem. Soc. 1970, 92, 2100.
38. D. A. Evans, G. C. Andrews, C. L. Sims, J Am. Chem. Soc. 1971, 93, 4956.
39. E. Block, S. Naganathan, D. Putman, S. H. Zhao, Pure Appl. Chem. 1993, 65, 625;
40. R. Bauer, W. Breu, H. Wagner, W. Weigand, J. Chromatogr. 1991, 541, 464.
41. J. Michalski, B. Mlotkowska, A. Skowronska, J. Chem. Soc., Perkin Trans, 1 1974, 319.
42. D. C. Morrison, J. Am. Chem. Soc. 1955, 77, 181.
43. A. K. Bhattacharya, G. Thyagarajan, Chem. Rev. 1981, 81, 415.
44. M. G. Blackburn, T. W. Maciej, J. Chem. Soc., Perkin Trans. 1 1985, 1419.
45. J. Chojnowski, M. Cypryk, W. Fortuniak, J. Michalski, Synthesis 1977, 683.
46. A. Skowrońska, R. Dembiński, R. Kamiński, J. Michalski, Tetrahedron Lett. 1987, 28, 4209.
47. K. A. Petrov, N. K. Bliznyuk, V. A. Savostenok, Zh. Obshch. Khim. 1961, 31, 1361;
48. Chem. Abstr. 1961, 55, 23317e.
49. G. Mlostoń, A. Majchrzak, M. Rutkowska, M. Woznicka, A. Linden, H. Heimgartner, Helv. Chim. Acta 2005, 88, 2624.
50. E. J. Corey, K. C. Nicolaou, J. Am. Chem. Soc. 1974, 96, 5614;
51. E. J. Corey, K. C. Nicolaou, L. S. Melvin Jr., J Am. Chem. Soc. 1975, 97, 653 and 654.
52. E. J. Corey, D. J. Brunelle, Tetrahedron Lett. 1976, 3409;
53. T. Sasaki, M. Inoue, M. Hirama, Tetrahedron Lett. 2001, 42, 5299.
54. R. Steudel, Chem. Rev. 2002, 102, 3905.
55. R. Steudel, K. Hassenberg, V. Münchow, O. Schumann, J. Pickard, Eur. J. Inorg. Chem. 2000, 92, 921.
56. A. Majchrzak, A. Janczak, G. Mlostoń, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 2272.
57. A. Majchrzak, G. Mlostoń, A. Linden, H. Heimgartner, Helv. Chim. Acta 2004, 87, 790.
58. I. L. Finar, A. J. Montgomery, J. Chem. Soc. 1961, 367.
59. R. P. Singh, J. M. Shreeve, Tetrahedron 2000, 56, 7613.
60. G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757.
61. G. Mlostoń, G. K. S. Prakash, G. A. Olah, H. Heimgartner, Helv. Chim. Acta 2002, 85, 1644.
62. I. V. Koval, T. G. Panasenko, Zh. Org. Khim. 1989, 25, 1677;
63. Chem. Abstr. 1990, 112, 197734.
64. G. Mlostoń, J. Romański, H. Heimgartner, Pol. J. Chem. 2001, 75, 975
65. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
66. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography; Part A, Eds. C. W. Carter Jr., R. M. Sweet, Academic Press, New York, 1997, p. 307.
67. R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33.
68. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, S1R92, J. Appl. Crystallogr. 1994, 27, 435.
69. H. D. Flack, G. Bernardinelli, Acta Crystallogr., Sect. A 1999, 55, 908;
70. H. D. Flack, G. Bernardinelli, J. Appl. Crystallogr. 2000, 33, 1143.
71. a) E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 6.1.1.1, p. 477;
72. b) D. C. Creagh, W. J. McAuley, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C. Table 4.2.6.8, p. 219;
73. c) D. C. Creagh, J. H. Hubbell, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 4.2.4.3, p. 200.
74. R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
75. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
76. G. M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures. University of Göttingen, Germany, 1997.