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Volumn 27, Issue 9, 2003, Pages 1377-1384

Cycloaddition of thiophene S-oxides to allenes, alkynes and to benzyne

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE; ALLENE DERIVATIVE; BENZOIC ACID DERIVATIVE; BENZYNE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFUR OXIDE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0142030148     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b303091c     Document Type: Article
Times cited : (35)

References (76)
  • 16
    • 0142108059 scopus 로고
    • (e) T. Thiemann, Y.-Q. Li, S. Mataka and M. Tashiro, J. Chem. Res. (S), 1995, 384; (M) 1995, 2364;
    • (1995) J. Chem. Res. (M) , pp. 2364
  • 26
    • 0001607816 scopus 로고    scopus 로고
    • (e) M. C. Suh and B. T. Jiang, Angew. Chem., 2000, 112, 2992; M. C. Suh and B. T. Jiang, Angew. Chem., 2000, 39, 2870.
    • (2000) Angew. Chem. , vol.112 , pp. 2992
    • Suh, M.C.1    Jiang, B.T.2
  • 27
    • 0034682917 scopus 로고    scopus 로고
    • (e) M. C. Suh and B. T. Jiang, Angew. Chem., 2000, 112, 2992; M. C. Suh and B. T. Jiang, Angew. Chem., 2000, 39, 2870.
    • (2000) Angew. Chem. , vol.39 , pp. 2870
    • Suh, M.C.1    Jiang, B.T.2
  • 32
    • 0000216705 scopus 로고
    • 2,5-Bis(tert-butyl)thiophene S-oxide was one of the very first thiophene S-oxides to be synthesized. In the original synthesis m-CPBA was used in absence of a Lewis acid the described yield was very low: W. L. Mock, J. Am. Chem. Soc., 1970, 92, 7610.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 7610
    • Mock, W.L.1
  • 41
    • 0142108057 scopus 로고    scopus 로고
    • M
    • (a) For commentary on the deoxygenation of thiophene S-oxides, see: ref. 1a and K. Kumazoe, K. Arima, S. Mataka, D. Walton and T. Thiemann, J. Chem. Res., 2003, (S) 60; (M) 248;
    • J. Chem. Res. , pp. 248
  • 49
    • 4243930835 scopus 로고    scopus 로고
    • (a) For a review on dibenzothiophene S-oxides, see: T. Thiemann, K. Arima and S. Mataka, Rep. Inst. Adv. Mat. Study Kyushu Univ., 2000, 14(1), 37-45; Chem. Abstr., 2001, 134, 173925u;
    • (2001) Chem. Abstr. , vol.134
  • 51
    • 85083593852 scopus 로고    scopus 로고
    • (b) for a review on benzothiophene S-oxides, see: T. Thiemann, K. Arima, K. Kumazoe and S. Mataka, Rep. Inst. Adv. Mat. Study Kyushu Univ., 2000, 14(2), 139-148; Chem. Abstr., 2001, 326, 134318a.
    • (2001) Chem. Abstr. , vol.326
  • 52
    • 0002470513 scopus 로고
    • 2-Methylbenzothiophene S-oxide (8) is a known material which had been synthesized previously from the corresponding benzothiophene by oxidation with p-nitroperoxybenzoic acid: P. Geneste, J. Grimaud, J. L. Olivé and S. N. Ung, Bull. Soc. Chim. Fr., 1977, 271.
    • (1977) Bull. Soc. Chim. Fr. , pp. 271
    • Geneste, P.1    Grimaud, J.2    Olivé, J.L.3    Ung, S.N.4
  • 57
    • 0001376012 scopus 로고    scopus 로고
    • for a review, see: A. S. Cieplak, Chem. Rev., 1999, 99, 1265.
    • (1999) Chem. Rev. , vol.99 , pp. 1265
    • Cieplak, A.S.1
  • 62
    • 0003975691 scopus 로고
    • Academic Press, New York
    • (a) For preparation and use of benzyne as dienophile, see: R. W. Hoffmann, Dehydrobenzenes and Cycloalkynes, Academic Press, New York, 1967, pp. 200;
    • (1967) Dehydrobenzenes and Cycloalkynes , pp. 200
    • Hoffmann, R.W.1
  • 65
    • 0142108052 scopus 로고    scopus 로고
    • note
    • The authors thank Prof. Dr. T. Kitamura of Saga University for a generous donation of 17.
  • 69
    • 0142108051 scopus 로고
    • (Engl.) and ref. cited
    • (b) V. D. Novokreshchennykh, S. S. Mochalov and Yu. S. Shabarov, Zh. Org. Khim., 1979, 15, 485 (Russ.) J. Org. Chem. USSR, 1979, 430 (Engl.) and ref. cited.;
    • (1979) J. Org. Chem. USSR , pp. 430
  • 72
    • 84982335329 scopus 로고
    • 13C NMR IR and MS. All new compounds gave correct analytical and/or HRMS data. A number of compounds had been synthesized before by alternative routes. For 6h and 6j see: W. Ried and K. Boenninghausen, Ann., 1961, 639, 61. For 6m see:D. CriegeeP. Ludwig, Chem. Ber., 1961, 94, 2038. For 6n see: J. Mueller and A. Huth, Tetrahedron Lett., 1972, 1035. For 6u, see: J. Novrocik, M. Novrocikova and J. Foniok, Collect. Czech Chem Commun., 1984, 49, 218.
    • (1961) Ann. , vol.639 , pp. 61
    • Ried, W.1    Boenninghausen, K.2
  • 73
    • 0013500545 scopus 로고
    • 13C NMR IR and MS. All new compounds gave correct analytical and/or HRMS data. A number of compounds had been synthesized before by alternative routes. For 6h and 6j see: W. Ried and K. Boenninghausen, Ann., 1961, 639, 61. For 6m see:D. CriegeeP. Ludwig, Chem. Ber., 1961, 94, 2038. For 6n see: J. Mueller and A. Huth, Tetrahedron Lett., 1972, 1035. For 6u, see: J. Novrocik, M. Novrocikova and J. Foniok, Collect. Czech Chem Commun., 1984, 49, 218.
    • (1961) Chem. Ber. , vol.94 , pp. 2038
    • Criegee, D.1    Ludwig, P.2
  • 74
    • 49649138819 scopus 로고
    • 13C NMR IR and MS. All new compounds gave correct analytical and/or HRMS data. A number of compounds had been synthesized before by alternative routes. For 6h and 6j see: W. Ried and K. Boenninghausen, Ann., 1961, 639, 61. For 6m see:D. CriegeeP. Ludwig, Chem. Ber., 1961, 94, 2038. For 6n see: J. Mueller and A. Huth, Tetrahedron Lett., 1972, 1035. For 6u, see: J. Novrocik, M. Novrocikova and J. Foniok, Collect. Czech Chem Commun., 1984, 49, 218.
    • (1972) Tetrahedron Lett. , pp. 1035
    • Mueller, J.1    Huth, A.2
  • 75
    • 0142076452 scopus 로고
    • 13C NMR IR and MS. All new compounds gave correct analytical and/or HRMS data. A number of compounds had been synthesized before by alternative routes. For 6h and 6j see: W. Ried and K. Boenninghausen, Ann., 1961, 639, 61. For 6m see:D. CriegeeP. Ludwig, Chem. Ber., 1961, 94, 2038. For 6n see: J. Mueller and A. Huth, Tetrahedron Lett., 1972, 1035. For 6u, see: J. Novrocik, M. Novrocikova and J. Foniok, Collect. Czech Chem Commun., 1984, 49, 218.
    • (1984) Collect. Czech Chem Commun. , vol.49 , pp. 218
    • Novrocik, J.1    Novrocikova, M.2    Foniok, J.3
  • 76
    • 0142108049 scopus 로고    scopus 로고
    • note
    • 4: 306.1831. Found: 306.1827.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.