Reactions of 5-Arylimino-4-chloro-5H-1,2,3-dithiazoles with Stable Phosphoranes: Novel Preparation of Dithiomethylenephosphoranes

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 869-872

  Lee, Hyi Seung ^a   Kim, Kyongtae ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 DITHIAZOLE DERIVATIVE; PHOSPHORANE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030030082     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02286-4     Document Type: Article

References (14)

1. (a) Appel, R.; Janssen, H.; Siray, M.; Knoch, F. Chem. Ber. 1985, 118, 1632.
2. (b) Oh, K. C.; Lee, H.: Kim, K. Tetrahedron Lett. 1992, 4963.
3. (c) Rees, C. W. J. Heterocycl. Chem. 1992, 29, 639.
4. (d) Folmer, J. J.; Weinreb, S. M. Tetrahedron Lett. 1993, 2737.
5. (a) Moore, J. E. U. S. Patent 4059590 1977; Chem. Abstr. 1978, 88, 50874.
6. (b) Mayer, R.; Foester, E.; Matauschek, B. Ger. (East) DD 212387, 1984; Chem. Abstr. 1985, 102, 1130645.
7. Lee, H.; Kim, K. J. Org. Chem. 1993, 58, 7001.
8. Lee, H.; Kim, K.; Whang, D.; Kim, K. J. Org. Chem. 1994, 59, 6179.
9. Unpublished results.
10. Denney, D. B.; Ross, S. T. J. Org. Chem. 1962, 27, 998.
11. Ramirez, F.; Dershowitz, S. J. Org. Chem. 1957, 22, 41.
12. Trippett, S.; Walker, D. M. J. Chem. Soc. 1959, 3874.
13. Lee, H.; Kim, K. Bull. Korean Chem. Soc. 1992, 13, 107.
14. -3, F(000) = 1112, Z = 4. X-ray intensity data were measured on an Enraf-Nonius CAD4 diffractometer with MoKα radiations with the dimension 0.97 x 0.45 x 0.37 mm. Of 4621 unique reflections measured, 4057 had I > 2.0σ(I) and were used for all calculations. The structure was solved by direct methods and refined by least-square methods. The final agreement factors were R = 0.049 and Rw = 0.048. All calculations and drawings were performed using a Micro VAX II computer with the MoIEN software. Selected bond lengths (Å) and angles (deg); S1-S2 2.134, S1-C3 1.699, P-C3 1.759, C2-C3 1.444, O-C2 1.240, C1-C2 1.516; S1-S2-C5 104.3, S2-S1-C3 106.9, S1-C3-P 119.6, S1-C3-C2 124.7, P-C3-C2 115.4, C3-P-C13 108.8, O-C2-C1 120.6, O-C2-C3 119.7, C1-C2-C3 119.7.