Evolution of functional cyclohexadiene-based synthetic reagents: The importance of becoming aromatic

Accounts of Chemical Research

Volumn 38, Issue 10, 2005, Pages 794-802

  Walton, John C ^a   Studer, Armido ^b  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 CYCLOHEXADIENE; 1,4-CYCLOHEXADIENE; ACID; AMIDE; AROMATIC HYDROCARBON; CYCLOHEXANE DERIVATIVE; CYCLOHEXENE DERIVATIVE; ESTER; STANNANE; TIN DERIVATIVE;

ARTICLE; CHEMISTRY; ELECTRON SPIN RESONANCE; KINETICS; METABOLISM; SYNTHESIS;

ACIDS; AMIDES; CYCLOHEXANES; CYCLOHEXENES; ELECTRON SPIN RESONANCE SPECTROSCOPY; ESTERS; HYDROCARBONS, AROMATIC; KINETICS; TIN COMPOUNDS;

EID: 27644476270     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar050089j     Document Type: Article

References (56)

1. Baguley, P. A.; Walton, J. C. Flight from the tyranny of tin: the quest for practical radical sources free from metal encumbrances. Angew. Chem., Int. Ed. 1998, 37, 3072-3082.
2. (a) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic: London, 1992.
3. (b) Renaud, P., Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2001; Vols. 1 and 2.
4. (c) Zard, S. Z. Radical Reactions in Organic Synthesis; Oxford University Press: Oxford, U.K., 2003.
5. (d) Togo, H. Advanced Free Radical Reactions for Organic Synthesis; Elsevier: Amsterdam, 2004.
6. Studer, A.; Amrein, S. Tin hydride substitutes in reductive radical chain reactions. Synthesis 2002, 835-849.
7. Laarhoven, L. J. J.; Mulder, P.; Wayner, D. D. M. Determination of bond dissociation enthalpies in solution by photoacoustic calorimetry. Acc. Chem. Res. 1999, 32, 342-349.
8. (a) Tsang, W. Thermodynamic and kinetic properties of the cyclohexadienyl radical. J. Phys. Chem. 1986, 90, 1152-1155.
9. (b) Ciriano, M. V.; Korth, H. G.; van Scheppingen, W. B.; Mulder, P. Thermal stability of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and related N-alkoxyamines. J. Am. Chem. Soc. 1999, 121, 6375-6381.
10. Binmore, G.; Walton, J. C.; Cardellini, L. Radical-chain decomposition of cyclohexa-1,4-diene-3-carboxylates and 2,5-dihydrofuran-2-carboxylates. J. Chem. Soc., Chem. Commun. 1995, 27-28.
11. Binmore, G.; Cardellini, L.; Walton, J. C. Alkyl radical generation using cyclohexa-1,4-diene-3-carboxylates and 2,5-dihydrofuran-2-carboxylates. J. Chem. Soc., Perkin Trans. 2 1997, 757-762.
12. (a) Baguley, P. A.; Binmore, G.; Milne, A.; Walton, J. C. Unique carbon-carbon bond homolysis in 3-alkylcyclohexa-1,4-dienyl-3-carboxylic acid radicals. Chem. Commun. 1996, 2199-2200.
13. (b) Baguley, P. A.; Walton, J. C. Reductive free-radical alkylation and cyclization mediated by 1-alkyl-2,5-cyclohexadiene-1-carboxylic acids. J. Chem. Soc., Perkin Trans. 1 1998, 2073-2082.
14. The low isolated yields of 14 and 15 in Scheme 3 were partly due to difficulties in separating and purifying the individual components.
15. Baguley, P. A.; Jackson, L. V.; Walton, J. C. Preparation of 1-phenylcyclohexa-2,5-diene-1-carboxylates and their use in free-radical mediated syntheses. J. Chem. Soc., Perkin Trans. 1 2002, 304-309.
16. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chemistry of acyl radicals. Chem. Rev. 1999, 99, 1991-2067.
17. (a) Jackson, L. V.; Walton, J. C. Generation of aminoacyl radicals from 1-carbamoyl-1-methylcyclohexa-2,5-dienes: a new tin-free homolytic route to β- and γ-lactams. Chem. Commun. 2000, 2327-2328.
18. (b) Bella, A. F.; Jackson, L. V.; Walton, J. C. Preparation of β- and -lactams via ring closures of unsaturated carbamoyl radicals derived from 1-carbamoyl-1-methylcyclohexa-2,5-dienes. Org. Biomol. Chem. 2004, 2, 421-428.
19. (a) Roberts, B. P. Polarity-reversal catalysis of hydrogen-atom abstraction reactions: concepts and applications in organic chemistry. Chem. Soc. Rev. 1999, 28, 25-35.
20. (b) Dang, H.-S.; Elsegood, M. R. J.; Kim, K.-M.; Roberts, B. P. Radical-chain reductive alkylation of electron-rich alkenes mediated by silanes in the presence of thiols as polarity-reversal catalysts. J. Chem. Soc., Perkin Trans. 1 1999, 2061-2068.
21. (c) Fielding A. J.; Roberts, B. P. Radical-chain isomerisation of allyl silyl ethers to silyl enol ethers in the presence of thiols as polarity reversal catalysts. Tetrahedron Lett. 2001, 42, 4061-4064.
22. Tomaszewski, M. J.; Warkentin, J.; Werstiuk, N. H. Free-radical chemistry of imines. Aust. J. Chem. 1995, 48, 291-321.
23. (a) Fallis, A. G.; Brinza, I. M. Free radical cyclizations involving nitrogen. Tetrahedron 1997, 53, 17543-17594.
24. (b) Friestad, G. K. Addition of carbon-centered radicals to imines and related compounds. Tetrahedron 2001, 57, 5461-5496.
25. (c) Naito, T. Heteroatom radical addition-cyclization and its synthetic application. Heterocycles 1999, 50, 505-541.
26. Bella, A. F.; Slawin, A. M. Z.; Walton, J. C. Approach to 3-amino-indolin-2-ones via oxime ether functionalized carbamoylcyclohexadienes. J. Org. Chem. 2004, 69, 5926-5933.
27. (a) Studer, A.; Amrein, S. Silylated cyclohexadienes: new alternatives to tributyltin hydride in free radical chemistry. Angew. Chem., Int. Ed. 2000, 39, 3080-3082.
28. (b) Studer, A.; Amrein, S.; Schleth, F.; Schulte, T.; Walton, J. C. Silylated cyclohexadienes as new radical chain reducing reagents: preparative and mechanistic aspects. J. Am. Chem. Soc. 2003, 125, 5726-5733.
29. Fettes, A.; Carreira, E. M. Formal total synthesis of leucascandrolide A. Angew. Chem., Int. Ed. 2002, 41, 4098-4101.
30. (a) Amrein, S.; Timmermann, A.; Studer, A. Radical transfer hydrosilylation/cyclization using silylated cyclohexadienes. Org. Lett. 2001, 3, 2357-2360.
31. (b) Amrein, S.; Studer, A. Silylated cyclohexadienes in radical chain hydrosilylations. Helv. Chim. Acta 2002, 85, 3559-3573.
32. Amrein, S.; Studer, A. Intramolecular radical hydrosilylation - the first radical 5-endo-dig cyclization. Chem. Commun. 2002, 1592-1593.
33. Neumann, W. P.; Hillgartner, H.; Baines, K. M.; Dicke, R.; Vorspohl, K.; Kobs, U.; Nussbeutel, U. New ways of generating organotin reactive intermediates for organic synthesis. Tetrahedron 1989, 45, 951-960.
34. Stella, L. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, p 407.
35. Müller, T. E.; Beller, M. Metal-initiated amination of alkenes and alkynes. Chem. Rev. 1998, 98, 675-703.
36. Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Advances and adventures in amination reactions of olefins and alkynes. Synlett 2002, 1579-1594.
37. Kemper, J.; Studer, A. New reagents for the generation of N-centered radicals - hydroamination of norbornene. Angew. Chem., Int. Ed. 2005, 44, 4914-4917.
38. Griller, D.; Ingold, K. U. Electron paramagnetic resonance and the art of physical-organic chemistry. Acc. Chem. Res. 1980, 13, 193-200.
39. Griller, D.; Ingold, K. U. Free-radical clocks. Acc. Chem. Res. 1980, 13, 317-323.
40. Schuh, H. H.; Fischer, H. The kinetics of the bimolecular self-reaction of tert-butyl radicals in solution. I. Termination rates. Helv. Chim. Acta 1978, 61, 2130-2164.
41. Fischer, H.; Paul, H. Rate constants for some prototype radical reactions in liquids by kinetic electron spin resonance. Acc. Chem. Res. 1987, 20, 200-206.
42. Maillard, B.; Walton, J. C. A kinetic electron spin resonance study of ring fission in methyl-substituted cyclobutylmethyl radicals. J. Chem. Soc., Perkin Trans. 2 1985, 443-450.
43. Jackson, L. V.; Walton, J. C. Homolytic dissociation of 1-substituted cyclohexa-2,5-diene-1-carboxylic acids: an EPR spectroscopic study of chain propagation. J. Chem. Soc., Perkin Trans. 2 2001, 1758-1764.
44. Bella, A. F.; Jackson, L. V.; Walton, J. C. A kinetic EPR study of the dissociation of 1-carbamoyl-1-methylcyclohexa-2,5-dienyl radicals: release of aminoacyl radicals and their cyclization. J. Chem. Soc., Perkin Trans. 2 2002, 1839-1843.
45. Walling, C.; Padwa, A. Positive halogen compounds. 6. Effects of structure and medium on â-scission of alkoxy radicals. J. Am. Chem. Soc. 1963, 85, 1593-1597.
46. Newcomb, M. Competition methods and scales for alkyl-radical reaction kinetics. Tetrahedron 1993, 49, 1151-1176.
47. Newcomb, M. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, p 317.
48. Effio, A.; Griller, D.; Ingold, K. U.; Scaiano, J. C.; Sheng, S. J. Studies on the spiro[2.5]octadienyl radical and the 2-phenylethyl rearrangement. J. Am. Chem. Soc. 1980, 102, 6063-6068.
49. Hawari, J. A.; Engel, P. S.; Griller, D. Rate constants for the reactions of alkyl radicals with 1,4-cyclohexadiene. Int. J. Chem. Kinet. 1985, 17, 1215-1219.
50. Newcomb, M.; Park, S. U. N-Hydroxypyridine-2-thione esters as radical precursors in kinetic studies. Measurements of rate constants for hydrogen-atom-abstraction reactions. J. Am. Chem. Soc. 1986, 108, 4132-4134.
51. Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. Rate constants and Arrhenius parameters for the reactions of primary, secondary, and tertiary alkyl radicals with tri-n-butyltin hydride. J. Am. Chem. Soc. 1981, 103, 7739-7742.
52. Chatgilialoglu, C.; Dickhaut, J.; Giese, B. Rate constants and Arrhenius parameters for the reactions of some carbon-centered radicals with tris(trimethylsilyl)silane. J. Org. Chem. 1991, 56, 6399-6403.
53. Lusztyk, J.; Maillard, B.; Lindsay, D. A.; Ingold, K. U. Rate constants and Arrhenius parameters for the reaction of a primary alkyl radical with tri-n-butylgermanium hydride. J. Am. Chem. Soc. 1983, 105, 3578-3580.
54. Baguley, P. A.; Walton, J. C. Thermal and induced decompositions of N-alkoxycarbonyldihydropyridines: end product analysis and EPR spectra of azacyclohexadienyl radicals. J. Chem. Soc., Perkin Trans. 2 1998, 1423-1429.
55. McCarroll, A. J.; Crayston, J. A.; Walton, J. C. Electron-transfer induced dissociations of 2- and 4-alkyl cyclohexadienones. Tetrahedron 2003, 59, 4275-4280.
56. Vaillard, S. E.; Postigo, A.; Rossi, R. A. Fast tin-free hydrodehalogenation and reductive radical cyclization reactions: A new reduction process. J. Org. Chem. 2004, 69, 2037-2041.