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Volumn 5, Issue 13, 2003, Pages 2195-2197

Photochemistry of diethynyl sulfides: A cycloaromatization for the formation of five-membered rings

Author keywords

[No Author keywords available]

Indexed keywords

1,4 CYCLOHEXADIENE; 2 PROPANOL; 2,5 DIDEHYDROTHIOPHENE; 3,4 DIPHENYLTHIOPHENE; ACETYLENE DERIVATIVE; ALCOHOL; ALKADIENE; BIS(PHENYLETHYNYL)SULFIDE; CARBON; HEXANE; PHENYLACETYLENE; SULFIDE; SULFUR; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0141629816     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034266x     Document Type: Article
Times cited : (32)

References (23)
  • 3
    • 0342517062 scopus 로고    scopus 로고
    • (a) Tour, J. M. Chem. Rev. 1996, 96, 537-553.
    • (1996) Chem. Rev. , vol.96 , pp. 537-553
    • Tour, J.M.1
  • 10
    • 0000770422 scopus 로고    scopus 로고
    • (b) Examples of nonaromatic five-membered ring cyclizations have been reported. For a review concerning the conversion of eneyne-allenes to fulvenes, see: Wang, K. K. Chem. Rev. 1996, 96, 207-222.
    • (1996) Chem. Rev. , vol.96 , pp. 207-222
    • Wang, K.K.1
  • 11
    • 0012960143 scopus 로고
    • (c) For a description of a diyne proceeding via a vinyl diradical, see: Zimmerman, H. E.; Pincock, J. A. J. Am. Chem. Soc. 1973, 95, 3246-3250.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 3246-3250
    • Zimmerman, H.E.1    Pincock, J.A.2
  • 12
    • 0006982548 scopus 로고
    • For isomeric didehydrothiophenes, see: (a) Reinecke, M. G. Tetrahedron 1982, 38, 427-498. (b) Teles, J. H.; Hess, B. A.; Schaad, L. J. Chem. Ber. 1992, 125, 423-431.
    • (1982) Tetrahedron , vol.38 , pp. 427-498
    • Reinecke, M.G.1
  • 13
    • 0005632546 scopus 로고
    • For isomeric didehydrothiophenes, see: (a) Reinecke, M. G. Tetrahedron 1982, 38, 427-498. (b) Teles, J. H.; Hess, B. A.; Schaad, L. J. Chem. Ber. 1992, 125, 423-431.
    • (1992) Chem. Ber. , vol.125 , pp. 423-431
    • Teles, J.H.1    Hess, B.A.2    Schaad, L.J.3
  • 20
    • 0000974225 scopus 로고    scopus 로고
    • (a) Higher temperatures led to a mixture of products consistent with a radical chain process where 4a was only a minor product. (b) Recently published computational results for enthalpies of the thermal cyclization depicted in Scheme 1b indicate a barrier of 55.8 kcal/mol and endothermicity of 19.3 kcal/mol: Kawatkar, S. P.; Schreiner, P. R. Org. Lett. 2002, 4, 3643-3646.
    • (2002) Org. Lett. , vol.4 , pp. 3643-3646
    • Kawatkar, S.P.1    Schreiner, P.R.2
  • 21
    • 0141439735 scopus 로고    scopus 로고
    • note
    • Photoirradiation of 2,5-diiodo-3,4-diphenylthiophene in hexanes in the absence of trapping agent exclusively yields 4a, indicating that formation of 5 or 7 from a thiophene monoradical is not facile.
  • 22
    • 0141662621 scopus 로고    scopus 로고
    • note
    • Vinyl diradical (8) is not trapped in the experiment, suggesting that either it does not form or that reactions competing with its trapping are more rapid than in the analogous hydrocarbon in ref 5c.
  • 23
    • 0028296555 scopus 로고
    • Acetylenic ether photochemistry has also been proposed to involve cleavage of the weaker heteroatom-carbon bond; see: Smith, B. A.; Callinan, A. J.; Swenton, J. S. Tetrahedron Lett. 1994, 35, 2283-2286.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 2283-2286
    • Smith, B.A.1    Callinan, A.J.2    Swenton, J.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.