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Volumn 11, Issue 16, 2009, Pages 3722-3725

An unexpectedly facile cyclization of polyhydric alcohols

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EID: 68949111600     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9013427     Document Type: Article
Times cited : (17)

References (37)
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    • for cyclization to an alkene in the presence of a catalytic amount of iodine. See
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    • Kim, K.M.1    Jeon, D.J.2    Ryu, E.K.3
  • 3
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    • For a list of reagents used to convert alcohols and phenols to ethers, see:, 2nd ed, Wiley-VCH, NY
    • (a) For a list of reagents used to convert alcohols and phenols to ethers, see: Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH, NY, 1999; pp 890-893.
    • (1999) Comprehensive Organic Transformations , pp. 890-893
    • Larock, R.C.1
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    • Scheuer, P. J, Ed, Academic: New York
    • (a) Moore, R. E. In Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. 1, pp 43-121.
    • (1978) Marine Natural Products , vol.1 , pp. 43-121
    • Moore, R.E.1
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    • Scheuer, P. J, Ed, Academic: New York
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    • and ref 13 therein. See
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    • Crimmins, M.T.1    DeBaillie, A.C.2
  • 29
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    • ORGN 101, Chemical Reactivity of Poly(ethylenedioxy)thiophene (PEDOT), Smith, M. B.; Sotzing, G. A.; Onorato, A.; Kumar, A.; Delude, C. 232nd ACS National Meeting, San Francisco, CA, September 10, 2006. 234th ACS National Meeting, Boston, MA, August 20, 2007.
    • (a) ORGN 101, Chemical Reactivity of Poly(ethylenedioxy)thiophene (PEDOT), Smith, M. B.; Sotzing, G. A.; Onorato, A.; Kumar, A.; Delude, C. 232nd ACS National Meeting, San Francisco, CA, September 10, 2006. 234th ACS National Meeting, Boston, MA, August 20, 2007.
  • 30
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    • ORGN 359, The Chemical Reactivity Of Sorbitol With PEDOT; Onorato, A.; Navarathne, D.; Smith, M. B.; Sotzing, G. A.
    • (b) ORGN 359, The Chemical Reactivity Of Sorbitol With PEDOT; Onorato, A.; Navarathne, D.; Smith, M. B.; Sotzing, G. A.
  • 37
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    • A catalytic amount of toluenesulfonic acid (1% mmol in 5 mL of toluene) was added to a solution of D-sorbitol (0.18 g, 1 mmol) in 60 mL of toluene via syringe, under a positive pressure of nitrogen. The solution was heated to reflux overnight and cooled, and the solution was treated with 10 mg of NaHCO3. The particulate matter was subsequently removed by filtration and washed with diethyl ether (10 mL, The toluene filtrate was concentrated in vacuo without heat to give 1,6-anhydrosorbitol 7 as a pale red waxy solid (129 mg, 0.786 mmol, 79, Mp, 29-30°C.1H NMR (CD 3OD):δ 4.54 (t, J, 4.7 Hz, 1H, 4.38 (d, J, 3.7 Hz, 1H, 4.28 (dt, J, 5.4, 6.9 Hz, 1H, 4.2 (s, 1H, 3.9-3.8 (m, 3H, 3.45 (dt, J, 7.5, 8.3 Hz, 1H, 13C NMR (CD3OD, δ 88.3, 81.9, 76.2, 75.2, 72.2, 71.4. MS (EI) m/z 164, 147, 129, 111-102, 87, 69
    • 3OD): δ 88.3, 81.9, 76.2, 75.2, 72.2, 71.4. MS (EI) m/z 164, 147, 129, 111-102, 87, 69.


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