Addition reactions of sulfenyl and sulfinyl chlorides with 3-phenyl-1-azabicyclo[1.1.0]butane

Helvetica Chimica Acta

Volumn 91, Issue 8, 2008, Pages 1419-1429

  Mlostoń, Grzegorz ^a   Woźnicka, Marta ^a   Drabowicz, Józef ^b   Linden, Anthony ^c   Heimgartner, Heinz ^c  

^a UNIVERSITY OF LODZ   (Poland)

^b CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

3 CHLORO 1 (ETHYLSULFINYL) 3 PHENYLAZETIDINE; 3 CHLORO 1 (METHYLSULFINYL) 3 PHENYLAZETIDINE; 3 CHLORO 1 [(1,1 DIMETHYLETHYL)SULFINYL] 3 PHENYLAZETIDINE; 3 CHLORO 1 [(1,1 DIMETHYLETHYL)SULFONYL] 3 PHENYLAZETIDINE; 3 CHLORO 3 [(3 CHLORO 3 PHENYLAZETIDIN 1 YL)SULFANYL] 2,2,4,4 TETRAMETHYLCYCLOBUTANONE; 3 CHLORO 3 [(3 CHLORO 3 PHENYLAZETIDIN 1 YL)SULFINYL] 2,2,4,4 TETRAMETHYLCYCLOBUTANONE; 3 CHLORO 3 [(3 CHLORO 3 PHENYLAZETIDIN 1 YL)SULFONYL] 2,2,4,4 TETRAMETHYLCYCLOBUTANONE; 3 CHLORO 3 PHENYL 1 (PHENYLSULFINYL)AZETIDINE; 3 CHLORO 3 PHENYL 1 (PHENYLSULFONYL)AZETIDINE; 3 CHLORO 3 PHENYL 1 [(1,3,3 TRICHLORO 2,2,4,4 TETRAMETHYLCYCLOBUTYL)SULFANYL]AZETIDINE; 3 CHLORO 3 PHENYL 1 [(1,3,3 TRICHLORO 2,2,4,4 TETRAMETHYLCYCLOBUTYL)SULFINYL]AZETIDINE; 3 CHLORO 3 PHENYL 1 [(1,3,3 TRICHLORO 2,2,4,4 TETRAMETHYLCYCLOBUTYL)SULFONYL]AZETIDINE; AZETIDINE; AZETIDINE DERIVATIVE; BUTANE; CARBON; CHLORIDE; NITROGEN; SULFENAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ATOM; CHEMICAL BOND; CRYSTAL STRUCTURE; PRIORITY JOURNAL; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 55449102212     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200890154     Document Type: Article

References (47)

1. R. Bartnik, A. P. Marchand, Synthesis 1997, 1029.
2. A. P. Marchand, A. Devasagayaraj, J. Org. Chem. 1997, 62, 4434.
3. G. Mlostoń, M. Celeda, Helv. Chim. Acta 2005, 88, 1658.
4. K. Itayashi, C. Sato, S. Itiki, T. Kumagai, Y. Nagao, Heterocycles 2002, 56, 433.
5. A. P. Marchand, G. V. Sharma, D. Rajagopal, R. Shukla, G. Mlostoń, R. Bartnik, J. Heterocycl. Chem. 1996, 33, 837.
6. A. P. Marchand, S. Hihodzic, R. Bartnik, G. Mlostoń, Heterocycles 1999, 50, 131.
7. R. Bartnik, S. Leśniak, A. Galindo, Pol. J. Chem. 1994, 68, 719.
8. A. P. Marchand, D. Rajagopal, S. Bott, T. G. Archibald, J. Org. Chem. 1994, 59, 1608.
9. A. Galindo, Ph.D. Thesis, University of Łódź, 1990.
10. K. Itayashi, C. Sato, S. Itiki, T. Kumagai, S. Tamai, T. Abe, Y. Nagao, Tetrahedron Lett. 1999, 40, 3761.
11. a) J. G. Tillett, in 'The Chemistry of Sulfinic Acids, Esters, and Their Derivatives', Ed. S. Patai, J. Wiley & Sons, Chichester, 1990, p. 577;
12. b) J. Drabowicz, P. Kiełbasiński, M. Mikołajczyk, in 'The Chemistry of Sulfenic Acids and Their Derivatives', Ed. S. Patai, J. Wiley & Sons, Chichester, 1990, p. 221;
13. c) J. Drabowicz, P. Kiełbasiński, P. Łyżwa, M. Mikołajczyk, in 'Science of Synthesis', Vol. 39, Ed. N. Kambe, Thieme, Stuttgart 2008, p. 543.
14. K. N. Koch, G. Mlostoń, A. Senning, Eur. J. Org. Chem. 1999, 83.
15. G. Mlostoń, A. Majchrzak, M. Rutkowska, M. Woźnicka, A. Linden, H. Heimgartner, Helv. Chim. Acta 2005, 88, 2624.
16. A. Majchrzak, G. Mlostoń, A. Linden, H. Heimgartner, Helv. Chim. Acta 2006, 89, 1042.
17. J. G. Tillet, in 'The Chemistry of Sulfinic Acids, Esters, and Their Derivatives', Ed. S. Patai, J. Wiley & Sons, Chichester, 1990, p. 603.
18. P. Zohn, B.-C. Chen, F. A. Davis, Tetrahedron 2004, 60, 8003;
19. K. Hiroi, T. Watanabe, Heterocycles 2001, 54, 73;
20. C. H. Senanayake, D. Krishnamurthy, Z.-H. Lu, Z. Han, I. Gallon, Aldrichimica Acta 2005, 38, 93.
21. D. Pei, Z. Wang, S. Wie, Y. Zhang, J. Sun, Org. Lett. 2006, 8, 5913.
22. J. C. Dore, J. Gilbert, T. Ojasoo, J. P. Raynaud, J. Med. Chem. 1986, 29, 54.
23. F. Sasse, D. Menche, Nat. Chem. Biol. 2007, 3, 87;
24. A. W. Pigott, P. Karuso, Tetrahedron Lett. 2007, 42, 7452.
25. I. V. Koval, Russ. Chem. Rev. 1996, 65, 421.
26. C. K. Johnson, 'ORTEP II, Report ORNL-5138', Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
27. M. Hesse, H. Meier, B. Zeeh, 'Spektroskopische Methoden in der organischen Chemie', 7th edn., Thieme, Stuttgart, 2005, p. 58.
28. I. B. Douglass, B. S. Farah, Org. Synth., Coll. Vol. V 1973, 709;
29. I. B. Douglass, R. V. Norton, J. Org. Chem. 1968, 33, 2104;
30. J. Drabowicz, B. Bujnicki, B. Dudzinski, Synth. Commun. 1994, 24, 1207.
31. H. G. Richey Jr., J. Farkas Jr., J. Org. Chem. 1987, 52, 479.
32. B. J. Wagner, J. T. Doi, W. K. Musker, J. Org. Chem. 1990, 55, 5940.
33. R. M. Moriarty, J. Org. Chem. 1963, 28, 1296;
34. R. M. Moriarty, Tetrahedron Lett. 1964, 5, 509.
35. A. G. Hortmann, D. A. Robertson, J. Am. Chem. Soc. 1972, 94, 2758.
36. H. Heimgartner, G. Mlostoń, 'Electronic Encyclopedia of Reagents in Organic Synthesis', Eds. L. Paquette, J. Rigby, D. Crich, P. Wipf, John Wiley & Sons, Chichester, Article RN00429.
37. H. Heimgartner, G. Mlostoń, 'Electronic Encyclopedia of Reagents in Organic Synthesis', Eds. L. Paquette, J. Rigby, D. Crich, P. Wipf, John Wiley & Sons, Chichester, Article RN00430.
38. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
39. 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.
40. R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33.
41. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435.
42. 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;
43. 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;
44. 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.
45. R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
46. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
47. G. M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen, 1997.