New cyclic dichalcogenonio-selenuranes induced by transannular multichalcogenides participation

Tetrahedron

Volumn 52, Issue 31, 1996, Pages 10375-10382

  Fujihara, Hisashi ^a   Mima, Hisatomo ^b   Furukawa, Naomichi ^b  

^a KINKI UNIVERSITY   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSELENIUM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030605910     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00583-2     Document Type: Article

References (17)

1. 1. For a review: Hayes, R. A.; Martin, J. C. 'Sulfurane Chemistry' In Organic Sulfur Chemistry, Theoretical and Experimental Advances; Bernardi, F.; Csizmadia, I. G.; Mangini, A., Eds.; Elsevier: Amsterdam, 1985; Chapter 8.
2. 2. (a) 'The Chemistry of Organic Selenium and Tellurium Compounds'; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1986; vol. 1, 1987; vol. 2. The term selenurane (selenane) has been used for tetracoordinate selenium (IV) compounds.
3. (b) 'Selenium Reagents and Intermediates in Organic Synthesis'; Paulmier, C. Pergamon Press, 1986.
4. 3. Fujihara, H.; Akaishi, R.; Erata, T.; Furukawa, N. J. Chem. Soc., Chem. Commun. 1989, 1789-1790; Iwasaki, F.; Morimoto, M.; Yasui, M.; Akaishi, R.; Fujihara, H.; Furukawa, N. Acta Crystallogr. 1991, C47, 1463-1466.
5. 3. Fujihara, H.; Akaishi, R.; Erata, T.; Furukawa, N. J. Chem. Soc., Chem. Commun. 1989, 1789-1790; Iwasaki, F.; Morimoto, M.; Yasui, M.; Akaishi, R.; Fujihara, H.; Furukawa, N. Acta Crystallogr. 1991, C47, 1463-1466.
6. 4. Fujihara, H.; Mima, H.; Erata, T.; Furukawa, N. J. Am. Chem. Soc. 1992, 114, 3117-3118.
7. 5. Gellatly, R. P.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans 1, 1976, 913-925; Brieaddy, L. E.; Hurlbert, B. S.; Mehta, N. B. J. Org. Chem. 1981, 46, 1630-1634.
8. 5. Gellatly, R. P.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans 1, 1976, 913-925; Brieaddy, L. E.; Hurlbert, B. S.; Mehta, N. B. J. Org. Chem. 1981, 46, 1630-1634.
9. 2Se.
10. B) is likely related to the Se-C-H dihedral angle.
11. 8. Iwasaki, F.; Toyoda, N.; Yamazaki, N.; Fujihara, H.; Furukawa, N. Acta Crystallogr., 1990, C46, 2154-2157.
12. 4 acts either as an oxidant or as a strong acid: Bard, A. J.; Ledwith, A.; Shine, H. J. Adv. Phys. Org. Chem., 1976, 12, 155.
13. 77Se NMR spectrum.
14. 11. Powell, R. L.; Hall, C. D. J. Am. Chem. Soc. 1969, 97, 5403-5404.
15. 12. Bodea, C.; Silberg, I. Adv. Heterocycl. Chem. 1968, 9, 321-460.
16. 13. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693-2698; Soderquist, J. A. Aldrichimica Acta, 1991, 24, 15-23.
17. 13. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693-2698; Soderquist, J. A. Aldrichimica Acta, 1991, 24, 15-23.