Rate constants for reaction of a fluorous tin hydride reagent with primary alkyl radicals

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2783-2786

  Horner, John H ^a   Martinez, Felix N ^a   Newcomb, Martin ^a   Hadida, Sabine ^b   Curran, Dennis P ^b  

^a WAYNE STATE UNIVERSITY   (United States)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; LASER; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0030980882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00489-9     Document Type: Article

References (18)

1. (a) Wayne State University.
2. (b) University of Pittsburgh.
3. (a) Hudlicky, M. Chemistry of Organic Fluorine Compounds; Ellis Horwood: Chichester, UK, 1992.
4. (b) Zhu, D.-W. Synthesis 1993, 953.
5. (c) Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
6. (d) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480.
7. (e) Studer, A.; Hadida, S.; Feritto; R.; Kim, S.-Y.; Jäger, P.; Wipf, P.; Curran, D. P., Science, in press.
8. Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. Tin hydride 1 is commercially available from Acros Organics.
9. (a) Johnson, C. C.; Horner, J. H.; Tronche, C.; Newcomb, M. J. Am. Chem. Soc. 1995, 117, 1684.
10. (b) Newcomb, M.; Horner, J. H.; Filipkowski, M. A.; Ha, C.; Park, S.-U. J. Am. Chem. Soc. 1995, 117, 3674.
11. (c) Tronche, C.; Martinez, F. N.; Horner, J. H.; Newcomb, M.; Senn, M.; Giese, B. Tetrahedron Lett. 1996, 37, 5845.
12. PTOC is an acronym for pyridine-2-thioneoxycarbonyl. PTOC esters are actually anhydrides of a carboxylic acid and the thiohydroxamic acid N-hydroxypyridine-2-thione. See: Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901.
13. 4c
14. For a discussion of interfering reactions in the LFP method, see: Musa, O. M.; Horner, J. H.; Shahin, H.; Newcomb, M. J. Am. Chem. Soc. 1996, 118, 3862.
15. Control experiments involving reaction of an alkyl radical with stannane 1 in the presence of acyclic product 6 demonstrated that hydrostannation was not appreciable.
16. Park, S.-U.; Chung, S.-K.; Newcomb, M. J. Am. Chem. Soc. 1986, 108, 240
17. T × Ms) = (9.06 ± 0.31) - (3.65 ± 0.41)/θ. See: Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739.
18. -1.