메뉴 건너뛰기




Volumn 5, Issue 2, 1999, Pages 759-773

The S(H)i reaction at silicon - A new entry into cyclic alkoxysilanes

Author keywords

Homolytic substitution reactions; Radical reactions; Silicon; Stereoselective reactions; Tin

Indexed keywords

RADICAL; SILANE DERIVATIVE; SILICON; TIN DERIVATIVE;

EID: 0033004828     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990201)5:2<759::AID-CHEM759>3.0.CO;2-V     Document Type: Article
Times cited : (39)

References (77)
  • 1
    • 33947465350 scopus 로고
    • K. Shiima, M. Kumada, J. Org. Chem. 1958, 23, 139; H. Sakurai, R. Koh, A. Hosomi, M. Kumada, Bull. Chem. Soc. Jpn. 1966, 39, 2050.
    • (1958) J. Org. Chem. , vol.23 , pp. 139
    • Shiima, K.1    Kumada, M.2
  • 4
    • 0026495242 scopus 로고
    • D. P. Curran, B. Yoo, Tetrahedron Lett. 1992, 33, 6931; see also: M. Ballestri, C. Chatgilialoglu, G. Seconi, J. Organomet. Chem. 1991, 408, C1.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6931
    • Curran, D.P.1    Yoo, B.2
  • 6
    • 0001516654 scopus 로고
    • M. Ballestri, C. Chatgilialoglu, M. Lucarini, G. F. Pedulli, J. Org. Chem. 1992, 57, 948; M. Lucarini, E. Marchesi, G. F. Pedulli, C. Chatgilialoglu, J. Org. Chem. 1998, 63, 1687; C. Chatgilialoglu, A. Guerrini, M. Lucarini, G. F. Pedulli, P. Carrozza, G. Da Roit, V. Borzatta, V. Lucchini, Organometallics 1998, 17, 2169.
    • (1992) J. Org. Chem. , vol.57 , pp. 948
    • Ballestri, M.1    Chatgilialoglu, C.2    Lucarini, M.3    Pedulli, G.F.4
  • 7
    • 0000108140 scopus 로고    scopus 로고
    • M. Ballestri, C. Chatgilialoglu, M. Lucarini, G. F. Pedulli, J. Org. Chem. 1992, 57, 948; M. Lucarini, E. Marchesi, G. F. Pedulli, C. Chatgilialoglu, J. Org. Chem. 1998, 63, 1687; C. Chatgilialoglu, A. Guerrini, M. Lucarini, G. F. Pedulli, P. Carrozza, G. Da Roit, V. Borzatta, V. Lucchini, Organometallics 1998, 17, 2169.
    • (1998) J. Org. Chem. , vol.63 , pp. 1687
    • Lucarini, M.1    Marchesi, E.2    Pedulli, G.F.3    Chatgilialoglu, C.4
  • 12
    • 0025855988 scopus 로고
    • Y.-M. Tsai, C.-D. Cherng, Tetrahedron Lett. 1991, 32, 3515; D. P. Curran, W.-T. Jiaang, M. Palovich, Y.-M. Tsai, Synlett 1993, 403; Y.-M. Tsai, K.-H. Tang, W.-T. Jiaang, Tetrahedron Lett. 1996, 37, 7767; S.-Y. Chang, W.-T. Jiaang, C.-D. Cherng, K.-H. Tang, C.-H. Huang, Y.-M. Tsai, J. Org. Chem. 1997, 62, 9089.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3515
    • Tsai, Y.-M.1    Cherng, C.-D.2
  • 13
    • 84952084052 scopus 로고
    • Y.-M. Tsai, C.-D. Cherng, Tetrahedron Lett. 1991, 32, 3515; D. P. Curran, W.-T. Jiaang, M. Palovich, Y.-M. Tsai, Synlett 1993, 403; Y.-M. Tsai, K.-H. Tang, W.-T. Jiaang, Tetrahedron Lett. 1996, 37, 7767; S.-Y. Chang, W.-T. Jiaang, C.-D. Cherng, K.-H. Tang, C.-H. Huang, Y.-M. Tsai, J. Org. Chem. 1997, 62, 9089.
    • (1993) Synlett , pp. 403
    • Curran, D.P.1    Jiaang, W.-T.2    Palovich, M.3    Tsai, Y.-M.4
  • 14
    • 0030597041 scopus 로고    scopus 로고
    • Y.-M. Tsai, C.-D. Cherng, Tetrahedron Lett. 1991, 32, 3515; D. P. Curran, W.-T. Jiaang, M. Palovich, Y.-M. Tsai, Synlett 1993, 403; Y.-M. Tsai, K.-H. Tang, W.-T. Jiaang, Tetrahedron Lett. 1996, 37, 7767; S.-Y. Chang, W.-T. Jiaang, C.-D. Cherng, K.-H. Tang, C.-H. Huang, Y.-M. Tsai, J. Org. Chem. 1997, 62, 9089.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7767
    • Tsai, Y.-M.1    Tang, K.-H.2    Jiaang, W.-T.3
  • 15
    • 0001286867 scopus 로고    scopus 로고
    • Y.-M. Tsai, C.-D. Cherng, Tetrahedron Lett. 1991, 32, 3515; D. P. Curran, W.-T. Jiaang, M. Palovich, Y.-M. Tsai, Synlett 1993, 403; Y.-M. Tsai, K.-H. Tang, W.-T. Jiaang, Tetrahedron Lett. 1996, 37, 7767; S.-Y. Chang, W.-T. Jiaang, C.-D. Cherng, K.-H. Tang, C.-H. Huang, Y.-M. Tsai, J. Org. Chem. 1997, 62, 9089.
    • (1997) J. Org. Chem. , vol.62 , pp. 9089
    • Chang, S.-Y.1    Jiaang, W.-T.2    Cherng, C.-D.3    Tang, K.-H.4    Huang, C.-H.5    Tsai, Y.-M.6
  • 16
    • 0000927845 scopus 로고    scopus 로고
    • S. Shuto, M. Kanazaki, S. Ichikawa, M. Minakawa, A. Matsuda, J. Org. Chem. 1998, 63, 746. However, in a recent computational study Schiesser concluded the intramolecular 1,2 silyl migration from carbon to carbon to be unlikely: C. H. Schiesser, M. L. Styles, J. Chem. Soc. Perkin Trans. 2 1997, 2335.
    • (1998) J. Org. Chem. , vol.63 , pp. 746
    • Shuto, S.1    Kanazaki, M.2    Ichikawa, S.3    Minakawa, M.4    Matsuda, A.5
  • 17
    • 0000748069 scopus 로고    scopus 로고
    • S. Shuto, M. Kanazaki, S. Ichikawa, M. Minakawa, A. Matsuda, J. Org. Chem. 1998, 63, 746. However, in a recent computational study Schiesser concluded the intramolecular 1,2 silyl migration from carbon to carbon to be unlikely: C. H. Schiesser, M. L. Styles, J. Chem. Soc. Perkin Trans. 2 1997, 2335.
    • (1997) J. Chem. Soc. Perkin Trans. 2 , pp. 2335
    • Schiesser, C.H.1    Styles, M.L.2
  • 20
    • 0011782110 scopus 로고
    • A. I. Prokof'ev, T. I. Prokof'eva, I. S. Belostotskaya, N. N. Bubnov, S. P. Solodovnikov, V. V. Ershov, M. I. Kabachnik, Tetrahedron 1979, 35, 2471; A. Alberti, A. Hudson, Chem. Phys. Lett. 1977, 48, 331; A. Alberti, C. Chatgilialoglu, Tetrahedron 1990, 46, 3963.
    • (1977) Chem. Phys. Lett. , vol.48 , pp. 331
    • Alberti, A.1    Hudson, A.2
  • 21
    • 0001701823 scopus 로고
    • A. I. Prokof'ev, T. I. Prokof'eva, I. S. Belostotskaya, N. N. Bubnov, S. P. Solodovnikov, V. V. Ershov, M. I. Kabachnik, Tetrahedron 1979, 35, 2471; A. Alberti, A. Hudson, Chem. Phys. Lett. 1977, 48, 331; A. Alberti, C. Chatgilialoglu, Tetrahedron 1990, 46, 3963.
    • (1990) Tetrahedron , vol.46 , pp. 3963
    • Alberti, A.1    Chatgilialoglu, C.2
  • 27
    • 0030583482 scopus 로고    scopus 로고
    • C. H. Schiesser, L. M. Wild, Tetrahedron 1996, 52, 13 265; C. H. Schiesser, M. L. Styles, L. M. Wild, J. Chem. Soc. Perkin Trans. 2 1996, 2257.
    • (1996) Tetrahedron , vol.52 , pp. 13265
    • Schiesser, C.H.1    Wild, L.M.2
  • 29
    • 0010372631 scopus 로고    scopus 로고
    • A. Studer, Angew. Chem. 1998, 110, 507; Angew. Chem. Int. Ed. 1998, 37, 462.
    • (1998) Angew. Chem. , vol.110 , pp. 507
    • Studer, A.1
  • 30
    • 0032473518 scopus 로고    scopus 로고
    • A. Studer, Angew. Chem. 1998, 110, 507; Angew. Chem. Int. Ed. 1998, 37, 462.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 462
  • 33
    • 0001031687 scopus 로고
    • c) A. Martinez-Grau, D. P. Curran, J. Org. Chem. 1995, 60, 8332; D. P. Curran, J. Xu, E. Lazzarini, J. Am. Chem. Soc. 1995, 117, 6603; A. Martinez-Grau, D. P. Curran, Tetrahedron 1997, 53, 5679;
    • (1995) J. Org. Chem. , vol.60 , pp. 8332
    • Martinez-Grau, A.1    Curran, D.P.2
  • 34
    • 0000664747 scopus 로고
    • c) A. Martinez-Grau, D. P. Curran, J. Org. Chem. 1995, 60, 8332; D. P. Curran, J. Xu, E. Lazzarini, J. Am. Chem. Soc. 1995, 117, 6603; A. Martinez-Grau, D. P. Curran, Tetrahedron 1997, 53, 5679;
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6603
    • Curran, D.P.1    Xu, J.2    Lazzarini, E.3
  • 35
    • 0030904327 scopus 로고    scopus 로고
    • c) A. Martinez-Grau, D. P. Curran, J. Org. Chem. 1995, 60, 8332; D. P. Curran, J. Xu, E. Lazzarini, J. Am. Chem. Soc. 1995, 117, 6603; A. Martinez-Grau, D. P. Curran, Tetrahedron 1997, 53, 5679;
    • (1997) Tetrahedron , vol.53 , pp. 5679
    • Martinez-Grau, A.1    Curran, D.P.2
  • 36
    • 0002868744 scopus 로고    scopus 로고
    • d) D. P. Curran, J. Xu, Synlett 1997, 1102. For other UMCTreactions see: G. E. Keck, E. J. Enholm, J. B. Yates, M. R. Wiley, Tetrahedron 1985, 41, 4079; S. Kim, J. S. Koh, J. Chem. Soc. Chem. Commun. 1992, 1377; J. Boivin, J. Camara, S. Z. Zard, J. Am. Chem. Soc. 1992, 114, 7909.
    • (1997) Synlett , pp. 1102
    • Curran, D.P.1    Xu, J.2
  • 37
    • 0000085277 scopus 로고
    • d) D. P. Curran, J. Xu, Synlett 1997, 1102. For other UMCTreactions see: G. E. Keck, E. J. Enholm, J. B. Yates, M. R. Wiley, Tetrahedron 1985, 41, 4079; S. Kim, J. S. Koh, J. Chem. Soc. Chem. Commun. 1992, 1377; J. Boivin, J. Camara, S. Z. Zard, J. Am. Chem. Soc. 1992, 114, 7909.
    • (1985) Tetrahedron , vol.41 , pp. 4079
    • Keck, G.E.1    Enholm, E.J.2    Yates, J.B.3    Wiley, M.R.4
  • 38
    • 37049070906 scopus 로고
    • d) D. P. Curran, J. Xu, Synlett 1997, 1102. For other UMCTreactions see: G. E. Keck, E. J. Enholm, J. B. Yates, M. R. Wiley, Tetrahedron 1985, 41, 4079; S. Kim, J. S. Koh, J. Chem. Soc. Chem. Commun. 1992, 1377; J. Boivin, J. Camara, S. Z. Zard, J. Am. Chem. Soc. 1992, 114, 7909.
    • (1992) J. Chem. Soc. Chem. Commun. , pp. 1377
    • Kim, S.1    Koh, J.S.2
  • 39
    • 0000556509 scopus 로고
    • d) D. P. Curran, J. Xu, Synlett 1997, 1102. For other UMCTreactions see: G. E. Keck, E. J. Enholm, J. B. Yates, M. R. Wiley, Tetrahedron 1985, 41, 4079; S. Kim, J. S. Koh, J. Chem. Soc. Chem. Commun. 1992, 1377; J. Boivin, J. Camara, S. Z. Zard, J. Am. Chem. Soc. 1992, 114, 7909.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7909
    • Boivin, J.1    Camara, J.2    Zard, S.Z.3
  • 43
    • 0344426470 scopus 로고    scopus 로고
    • note
    • 3.
  • 44
    • 0344858276 scopus 로고    scopus 로고
    • note
    • 3 with subsequent chlorodeamination according to ref. [20]. The stannylated chlorosilane was isolated in 60% purity.
  • 45
    • 0344426469 scopus 로고    scopus 로고
    • note
    • 3SiH over three steps (see Experimental Section). The chlorosilane was not easily purified and was used in 60-80% purity for the subsequent silylation reaction.
  • 46
    • 33845558052 scopus 로고
    • For a compilation of Si-Si bond energies see: R. Walsh. Acc. Chem. Res. 1981, 14, 246.
    • (1981) Acc. Chem. Res. , vol.14 , pp. 246
    • Walsh, R.1
  • 51
    • 0345721158 scopus 로고    scopus 로고
    • note
    • 6 and analysed prior to the removal of the solvent.
  • 52
    • 0032569916 scopus 로고    scopus 로고
    • For 9 and 11 small amounts of an arylated side product were observed; this was formed by a 1,5-phenyl transfer from silicon to carbon. With secondary radicals this aryl transfer is the main reaction: A. Studer, M. Bossart, H. Steen, Tetrahedron Lett. 1998, 39, 8829.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8829
    • Studer, A.1    Bossart, M.2    Steen, H.3
  • 53
    • 0345289581 scopus 로고    scopus 로고
    • note
    • Silyl ethers derived from primary alcohols cyclize much slower than their congeners derived from secondary or tertiary alcohols (see below). For the fast cyclizing systems it was difficult to isolate pure radical precursors, because traces of an initiator can start the UMCT reaction and thus lead to decomposition of the starting material.
  • 56
    • 0344858270 scopus 로고    scopus 로고
    • note
    • 3).
  • 59
    • 0344858269 scopus 로고    scopus 로고
    • note
    • All the compounds were prepared as racemic mixtures.
  • 60
    • 0345289579 scopus 로고    scopus 로고
    • note
    • The relative configuration was assigned after transformation of 33 to the corresponding known diol derivative by Tamao-Fleming oxidation, see below. 3-Phenyl-2-pentanol (35%, u:l = 10:1) was formed as the main product. This product derives from a stereoselective 1,5 phenyl transfer from Si to C with subsequent desilylation: A. Studer, M. Bossart, H. Steen, réf. [21].
  • 61
    • 0345289580 scopus 로고    scopus 로고
    • note
    • The sun lamp was placed very close to the reaction vessel (sealed tube, T> 100°C). The relative configuration was assigned in analogy.
  • 62
    • 0345289578 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-102599 (trans-41). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam. ac.uk). The X-ray analysis was carried out by Dr. V. Gramlich (ETH Zürich).
  • 63
    • 33748939157 scopus 로고
    • R. M. Beesley, C. K. Ingold, J. F. Thorpe, J. Chem. Soc. 1915, 107, 1080; M. E. Jung, J. Gervay, J. Am. Chem. Soc. 1991, 113, 224; A. L. Parrill, D. P. Dolata, Tetrahedron Lett. 1994, 35, 7319; M. E. Jung, M. Kiankarimi, J. Org. Chem. 1998, 63, 2968.
    • (1915) J. Chem. Soc. , vol.107 , pp. 1080
    • Beesley, R.M.1    Ingold, C.K.2    Thorpe, J.F.3
  • 64
    • 0001609007 scopus 로고
    • R. M. Beesley, C. K. Ingold, J. F. Thorpe, J. Chem. Soc. 1915, 107, 1080; M. E. Jung, J. Gervay, J. Am. Chem. Soc. 1991, 113, 224; A. L. Parrill, D. P. Dolata, Tetrahedron Lett. 1994, 35, 7319; M. E. Jung, M. Kiankarimi, J. Org. Chem. 1998, 63, 2968.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 224
    • Jung, M.E.1    Gervay, J.2
  • 65
    • 0028095190 scopus 로고
    • R. M. Beesley, C. K. Ingold, J. F. Thorpe, J. Chem. Soc. 1915, 107, 1080; M. E. Jung, J. Gervay, J. Am. Chem. Soc. 1991, 113, 224; A. L. Parrill, D. P. Dolata, Tetrahedron Lett. 1994, 35, 7319; M. E. Jung, M. Kiankarimi, J. Org. Chem. 1998, 63, 2968.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7319
    • Parrill, A.L.1    Dolata, D.P.2
  • 66
    • 0001392294 scopus 로고    scopus 로고
    • R. M. Beesley, C. K. Ingold, J. F. Thorpe, J. Chem. Soc. 1915, 107, 1080; M. E. Jung, J. Gervay, J. Am. Chem. Soc. 1991, 113, 224; A. L. Parrill, D. P. Dolata, Tetrahedron Lett. 1994, 35, 7319; M. E. Jung, M. Kiankarimi, J. Org. Chem. 1998, 63, 2968.
    • (1998) J. Org. Chem. , vol.63 , pp. 2968
    • Jung, M.E.1    Kiankarimi, M.2
  • 68
    • 0030800688 scopus 로고    scopus 로고
    • S.-U. Park, T. R. Varick, M. Newcomb, Tetrahedron Lett. 1990, 31, 2975; M. E. Jung, R. Marquez, Tetrahedron Lett. 1997, 38, 6521.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6521
    • Jung, M.E.1    Marquez, R.2
  • 70
    • 0030838363 scopus 로고    scopus 로고
    • T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230; Angew. Chem. Int. Ed. Engt. 1997, 36, 1181.
    • (1997) Angew. Chem. Int. Ed. Engt. , vol.36 , pp. 1181
  • 74
    • 0001566548 scopus 로고
    • M. Bols, T. Skrydstrup, Chem. Rev. 1995, 95, 1253; L. Fensterbank, M. Malacria, S. McN. Sieburth, Synthesis 1997, 813.
    • (1995) Chem. Rev. , vol.95 , pp. 1253
    • Bols, M.1    Skrydstrup, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.