Tin-free radical cyclization reactions using the persistent radical effect

Angewandte Chemie - International Edition

Volumn 39, Issue 6, 2000, Pages 1108-1111

  Studer, Armido ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Cyclizations; Isomerizations; Oxygenations; Radical reactions; Synthetic methods

Indexed keywords

ORGANOTIN COMPOUND; RADICAL;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; POLYMERIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; TEMPERATURE;

EID: 0034678011     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000317)39:6<1108::AID-ANIE1108>3.0.CO;2-A     Document Type: Article

References (55)

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31. 2O, THF).
32. CSA was also used as an additive in SFRP: M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, G. K. Hamer, M. Saban, Macromolecules 1994, 27, 7228; P. G. Odell, R. P. N. Veregin, L. M. Michalak, D. Brousmiche, M. K. Georges, Macromolecules 1995, 28, 8453; R. P. N. Veregin, P. G. Odell, L. M. Michalak, M. K. Georges, Macromolecules 1996, 29, 4161; M. V. Baldovi, N. Mohtat, J. C. Scaiano, Macromolecules 1996, 29, 5497; T. J. Conolly, J. C. Scaiano. Tetrahedron Lett. 1997, 38, 1133.
33. CSA was also used as an additive in SFRP: M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, G. K. Hamer, M. Saban, Macromolecules 1994, 27, 7228; P. G. Odell, R. P. N. Veregin, L. M. Michalak, D. Brousmiche, M. K. Georges, Macromolecules 1995, 28, 8453; R. P. N. Veregin, P. G. Odell, L. M. Michalak, M. K. Georges, Macromolecules 1996, 29, 4161; M. V. Baldovi, N. Mohtat, J. C. Scaiano, Macromolecules 1996, 29, 5497; T. J. Conolly, J. C. Scaiano. Tetrahedron Lett. 1997, 38, 1133.
34. CSA was also used as an additive in SFRP: M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, G. K. Hamer, M. Saban, Macromolecules 1994, 27, 7228; P. G. Odell, R. P. N. Veregin, L. M. Michalak, D. Brousmiche, M. K. Georges, Macromolecules 1995, 28, 8453; R. P. N. Veregin, P. G. Odell, L. M. Michalak, M. K. Georges, Macromolecules 1996, 29, 4161; M. V. Baldovi, N. Mohtat, J. C. Scaiano, Macromolecules 1996, 29, 5497; T. J. Conolly, J. C. Scaiano. Tetrahedron Lett. 1997, 38, 1133.
35. CSA was also used as an additive in SFRP: M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, G. K. Hamer, M. Saban, Macromolecules 1994, 27, 7228; P. G. Odell, R. P. N. Veregin, L. M. Michalak, D. Brousmiche, M. K. Georges, Macromolecules 1995, 28, 8453; R. P. N. Veregin, P. G. Odell, L. M. Michalak, M. K. Georges, Macromolecules 1996, 29, 4161; M. V. Baldovi, N. Mohtat, J. C. Scaiano, Macromolecules 1996, 29, 5497; T. J. Conolly, J. C. Scaiano. Tetrahedron Lett. 1997, 38, 1133.
36. CSA was also used as an additive in SFRP: M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, G. K. Hamer, M. Saban, Macromolecules 1994, 27, 7228; P. G. Odell, R. P. N. Veregin, L. M. Michalak, D. Brousmiche, M. K. Georges, Macromolecules 1995, 28, 8453; R. P. N. Veregin, P. G. Odell, L. M. Michalak, M. K. Georges, Macromolecules 1996, 29, 4161; M. V. Baldovi, N. Mohtat, J. C. Scaiano, Macromolecules 1996, 29, 5497; T. J. Conolly, J. C. Scaiano. Tetrahedron Lett. 1997, 38, 1133.
37. [14] was formed in very low yield (<2%) under our conditions.
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40. The ESR experiments were carried out in the laboratory of Prof. Hanns Fischer at the University of Zürich. For experimental reasons the reactions were conducted in tBuOH/tBuPh (1/1). We also performed the isomerization under the conditions applied in the ESR experiment. Clean but slower isomerization was observed in tBuOH/tBuPh (1/1) without the use of CSA. Experimental details are given in: S. Marque, C. Le Mercier, P. Tordo, H. Fischer, Macromolecules, submitted.
41. The 6-endo products also formed in the cyclization are omitted in Scheme 2 for reasons of clarity. For similar cross-over experiments in polymerizations, see: C. J. Hawker, Acc. Chem. Res. 1997, 30, 373.
42. 2) in the presence of TEMPO (36%).
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45. The relative configuration of 15a-d was assigned in analogy to that of 4.
46. [28] in an analogous manner. In the isomerizations of 18-22 the corresponding cyclized compounds (5-exo and 6-endo) were obtained in high yields (>60%).
47. While we were carrying out our experiments, similar alkoxyamines were suggested for SFRP : D. Benoit, V. Chaplinski, R. Braslau, C. J. Hawker, J. Am. Chem. Soc. 1999, 121, 3904. The nitroxides were prepared in analogy.
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50. Intramolecular hydrogen bonding has already been suggested: E. G. Janzen, J. I-Ping Liu, J. Magn. Reson. 1973, 9, 510.
51. Due to the complex NMR spectra, the 5-exo:6-endo ratio was not determined.
52. The synthesis of 30 (d.r.=1:1, racemic) is described in the Supporting Information.
53. D. P. Curran, S.-C. Kuo, J. Am. Chem. Soc. 1986, 108, 1106; A. Matzeit, H. J. Schäfer, C. Amatore, Synthesis 1995, 1432.
54. D. P. Curran, S.-C. Kuo, J. Am. Chem. Soc. 1986, 108, 1106; A. Matzeit, H. J. Schäfer, C. Amatore, Synthesis 1995, 1432.
55. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-137891. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).