Alkylthiylation of triquinphosphoranes by disulfides: An entry to chiral thiatriquinphosphoranes

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3073-3076

  Marchi, Caroline ^a   Buono, Geérard ^a  

^a CNRS   (France)

Author keywords

Alkylthiylation; Chirality; Phosphoranes

Indexed keywords

DISULFIDE; FREE RADICAL; PHOSPHORANE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ULTRAVIOLET IRRADIATION;

EID: 0034701515     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00338-5     Document Type: Article

References (18)

1. (a) Burgada, R.; Setton, R. Preparation, properties and reactions of phosphoranes. In The Chemistry of Organophosphorus Compounds; Hartley, F. R.; Patai, S., Eds.; J. Wiley & Sons: New York, 1994; Vol. 3, p. 185.
2. (b) Holmes, R. R. In Pentacoordinated Phosphorus - Structure and Spectroscopy; ACS Monograph 175; American Chemical Society, Washington, 1980; Vol. 1.
3. (c) Gavrilov, K. N.; Mikhel', I. S. Russian Chem. Rev. 1996, 65, 225-247.
4. For reviews on the formation, structures, and reactions of phosphoranyl radicals, see: (a) Bentrude, W. G. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum: London, 1983; Vol. 3, pp. 199-298.
5. (b) Bentrude, W. G. Acc. Chem. Res. 1982, 15, 117.
6. (c) Roberts, B. P. In Advances in Free Radical Chemistry; Williams, G. H., Ed.; Heyden & Sons: London, 1980; Vol. 6, pp. 225-289.
7. (a) Bentrude, W. G.; Del Alley, W.; Johnson, N. A.; Murakami, M.; Nishikida, K.; Tan, H. W. J. Am. Chem. Soc. 1977, 99, 4383.
8. (b) Bentrude, W. G.; Kawashima, T.; Keys, B. A.; Garroussian, M.; Heide, W.; Wedegaertner, D. A. J. Am. Chem. Soc. 1987, 109, 1227-1235.
9. (a) Bojin, M. L.; Barkallah, S.; Evans S. A. Jr., J. Am. Chem. Soc. 1996, 118, 1549-1550.
10. (b) Kojima, S.; Takagi, R.; Akiba, K.-Y. J. Am. Chem. Soc. 1997, 119, 5970-5971.
11. (a) Vannoorenberghe, Y.; Buono, G. J. Am. Chem. Soc. 1990, 112, 6142-6143.
12. (b) Marchi, C.; Fotiadu, F.; Buono, G. Organometallics 1999, 18, 915-927.
13. (c) Marchi, C.; Buono, G. Tetrahedron Lett. 1999, 40, 9251-9254.
14. 1,5]undecane were synthesised from diaminodiols N, N′-(bis(hydroxyethyl)ethylenediamine and (2S,7S)-2,7-dibenzyl-3,6-diazaocta-1,8-diol, respectively, see: Ref. 4b.
15. 8): δ -14.3 ppm.
16. 8): δ 53.9 ppm.
17. Original Hanau system, with a Hg lamp.
18. 3).