Tris(trimethylsilyl)silane as mediator in the radical-based allylation reactions of allyl and 2-functionalized allyl phenyl sulfones

Tetrahedron Letters

Volumn 37, Issue 35, 1996, Pages 6391-6394

  Chatgilialoglu, Chryssostomos ^a   Alberti, Angelo ^a   Ballestri, Marco ^a   Macciantelli, Dante ^a   Curran, Dennis P ^b  

^a CNR   (Italy)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; SULFONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030603062     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01355-X     Document Type: Article

References (12)

1. 1. For Y = SPh, see: (a) Keck, G. E.; Byers, J. H. J. Org. Chem. 1985, 50, 5442.
2. (b) Curran, D. P.; Yoo, B. Tetrahedron Lett. 1992, 33, 6931.
3. 2Ph, see: Keck, G. E.; Tafesh, A. M. J. Org. Chem. 1989, 54, 5845.
4. 3. For Y = Cl, see: Huval, C. C.; Singleton, A. A. Tetrahedron Lett. 1993, 34, 3041.
5. 4. For other systems involving allyl sulfones as allylating agents, see: (a) Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209.
6. (b) Phillips, E. D.; Whitham, G. H. Tetrahedron Lett. 1993, 34, 2537.
7. 5. Newcomb, M. Tetrahedron 1993, 49, 1151.
8. 6. Chatgilialoglu, C. In The Chemistry of Sulphones and Sulphoxides; Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds.; Wiley: Chichester, 1988; pp 1081-1113.
9. 7. Tetrahydrofuranyl and tert-butyl radicals were obtained by photolysis of di-tert-butyl peroxide in THF and photolysis of di-terf-butyl ketone in methyl ether, respectively.
10. 8. Chatgilialoglu, C.; Gilbert, B. C.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1979, 770.
11. 9. Weil, J. A.; Bolton, J. R.; Wertz, J. E. Electron Paramagnetic Resonance: Elementary Theory and Practical Applications; Wiley: New York, 1994.
12. 10. Strub, W.; Roduner, E.; Fischer, H. J. Phys. Chem. 1987, 91, 4379.