An expeditious one-pot synthesis of thiiranes from α-halo ketones in solvent-free conditions using microwaves

Synthesis

Volumn , Issue 16, 2002, Pages 2344-2346

  Yadav, Lal Dhar S ^a   Kapoor, Ritu ^a  

^a UNIVERSITY OF ALLAHABAD   (India)

Author keywords

Alumina supported; Microwaves; Solvent free; Stereoselective synthesis; Thiiranes; haloketones

Indexed keywords

IRRADIATION; MICROWAVES; SOLVENTS; SYNTHESIS (CHEMICAL);

DIASTEREOSELECTIVITY;

KETONES;

ALUMINUM OXIDE; HALOKETONE; HETEROCYCLIC COMPOUND; O,O DIETHYL HYDROGEN PHOSPHORODITHIOATE; PHOSPHOROTHIOIC ACID DERIVATIVE; SODIUM BOROHYDRIDE; SOLVENT; SULFUR DERIVATIVE; THIIRANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MICROWAVE IRRADIATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036437557     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35222     Document Type: Article

References (20)

1. For reviews, see: (a) Dittmer, D. C. Thiiranes and thiirenes In Comprehensive Heterocyctic Chemistry, Vol. 7; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Elmsford NY, 1984, 132. (b) Kamal, J. In Second Supplement to the 2nd Edition of Rodds Chemistry of Carbon Compounds Vol. IV A; Sainsbury, A., Ed.; Elsevier Science B. V.: Amsterdam, 1997, 49. (c) Reynolds, D. D.; Fields, D. L. In The Chemistry of Heterocyclic Compounds, Vol. 19, Part 1; Weissberger, A., Ed.; John Wiley and Sons Inc.: New York, 1964, 576.
2. For reviews, see: (a) Dittmer, D. C. Thiiranes and thiirenes In Comprehensive Heterocyctic Chemistry, Vol. 7; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Elmsford NY, 1984, 132. (b) Kamal, J. In Second Supplement to the 2nd Edition of Rodds Chemistry of Carbon Compounds Vol. IV A; Sainsbury, A., Ed.; Elsevier Science B. V.: Amsterdam, 1997, 49. (c) Reynolds, D. D.; Fields, D. L. In The Chemistry of Heterocyclic Compounds, Vol. 19, Part 1; Weissberger, A., Ed.; John Wiley and Sons Inc.: New York, 1964, 576.
3. For reviews, see: (a) Dittmer, D. C. Thiiranes and Thiirenes In Comprehensive Heterocyctic Chemistry, Vol. 7; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Elmsford NY, 1984, 132. (b) Kamal, J. In Second Supplement to the 2nd Edition of Rodds Chemistry of Carbon Compounds Vol. IV A; Sainsbury, A., Ed.; Elsevier Science B. V.: Amsterdam, 1997, 49. (c) Reynolds, D. D.; Fields, D. L. In The Chemistry of Heterocyclic Compounds, Vol. 19, Part 1; Weissberger, A., Ed.; John Wiley and Sons Inc.: New York, 1964, 576.
4. Dittmer, D. C. Thiiranes and thiirenes In Comprehensive Heterocyclic Chemistry, Vol. 7; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Elmsford NY, 1984, 182.
5. Knapp, S.; Malolanarasimhan, K. Org. Lett. 1999, 1, 611.
6. Sloan, A. D. B. J. Chem. Soc. D 1969, 1252.
7. Kihara, N.; Nakawaki, Y.; Endo, T. J. Org. Chem. 1995, 60, 473; and references therein.
8. Meyers, A. I.; Ford, M. E. J. Org. Chem. 1976, 41, 1735.
9. Takata, T.; Endo, T. Bull. Chem. Soc. Jpn. 1988, 61, 1818.
10. (a) Caddick, S. Tetrahedron 1995, 51, 10403.
11. (b) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
12. (c) Varma, R. S. Green Chem. 1999, 1, 43.
13. Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
14. Varma, R. S.; Saini, R. K. Tetrahedron Lett. 1997, 38, 4337.
15. (a) Yadav, L. D. S.; Sharma, S. Synthesis 1993, 864.
16. (b) Yadav, L. D. S.; Vaish, A. J. Chem. Res. Synop. 1993, 508.
17. (c) Ueno, Y.; Yadav, L. D. S.; Okawara, M. Synthesis 1981, 547.
18. Raner, K. D.; Strauss, C. R.; Vyskoc, F.; Mokbel, L. J. Org. Chem. 1993, 58, 950.
19. Buter, J.; Wassenaar, S.; Kellogg, R. M. J. Org. Chem. 1972, 37, 4045; and references therein.
20. Neureiter, N. P.; Bordwell, F. G. J. Am. Chem. Soc. 1959, 81, 578.