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Volumn 108, Issue 6, 2008, Pages 2051-2063

The Dehydro-Diels - Alder reaction

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; AROMATIC COMPOUNDS; BENZENE; CHEMICAL REACTIONS; HYDROCARBONS; HYDROGEN; NONMETALS; OLEFINS;

EID: 47249130867     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr0783986     Document Type: Article
Times cited : (308)

References (148)
  • 1
    • 0003497902 scopus 로고    scopus 로고
    • Kobayashi, S, Jørgensen, K. A, Eds, Wiley-VCH: Weinheim
    • Kobayashi, S., Jørgensen, K. A., Eds. Cycloaddition Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2002.
    • (2002) Cycloaddition Reactions in Organic Synthesis
  • 7
  • 17
    • 47249103744 scopus 로고
    • (a) Lanser, Th. Chem. Ber. 1899, 32, 2479.
    • (1899) Chem. Ber , vol.32 , pp. 2479
    • Lanser, T.1
  • 20
  • 91
    • 0030724760 scopus 로고    scopus 로고
    • The analogous intramolecular variant of this reaction was observed upon pyrolysis of nona-1,3,8-triyne: Bradley, A. Z.; Johnson, R. P. J. Am. Chem. Soc. 1997, 119, 9917.
    • (c) The analogous intramolecular variant of this reaction was observed upon pyrolysis of nona-1,3,8-triyne: Bradley, A. Z.; Johnson, R. P. J. Am. Chem. Soc. 1997, 119, 9917.
  • 112
    • 47249115628 scopus 로고    scopus 로고
    • We have performed a multiconfiguration SCF calculation CASS-CF10,10/ 6-31G≤ of benzo[fleyclohexa-1,2,4-triene the parent hydrocarbon of 103 and found that this molecule is best described as a closed shell species with certain diradical character and that the HOMO consists mainly of the lone pair at C-4. This explains why 103 does not react with typical hydrogen donors, such as cyclohexa-1,4-diene, as mentioned in ref 50b
    • We have performed a multiconfiguration SCF calculation CASS-CF10,10/ 6-31G≤ of benzo[fleyclohexa-1,2,4-triene the parent hydrocarbon of 103 and found that this molecule is best described as a closed shell species with certain diradical character and that the HOMO consists mainly of the lone pair at C-4. This explains why 103 does not react with typical hydrogen donors, such as cyclohexa-1,4-diene, as mentioned in ref 50b.
  • 124
    • 34249927653 scopus 로고    scopus 로고
    • Further examples of DDA reactions of ammonium salts catalyzed by bases: Chukhadzhyan, É. O.; Chukhadzhyan, Él. O.; Shakhatuni, K. G.; Babayan, A. T. Chem. Heterocycl. Compd. 1991, 27, 594.
    • (a) Further examples of DDA reactions of ammonium salts catalyzed by bases: Chukhadzhyan, É. O.; Chukhadzhyan, Él. O.; Shakhatuni, K. G.; Babayan, A. T. Chem. Heterocycl. Compd. 1991, 27, 594.
  • 133
    • 0141512766 scopus 로고    scopus 로고
    • The DDA cyclization of the diol corresponding to the dione 126 was described by Straub and Hambrecht: Straub, H.; Hambrecht, J. Synthesis 1975, 425.
    • (c) The DDA cyclization of the diol corresponding to the dione 126 was described by Straub and Hambrecht: Straub, H.; Hambrecht, J. Synthesis 1975, 425.
  • 135
    • 0030004398 scopus 로고    scopus 로고
    • Baidossi, W.; H. Schumann, H.; Blum, J. Tetrahedron 1996, 52, 8349.
    • (b) Baidossi, W.; H. Schumann, H.; Blum, J. Tetrahedron 1996, 52, 8349.
  • 136
    • 0025456530 scopus 로고    scopus 로고
    • 3/Aliquat 336 catalyst: Amer, L.; Blum, J.; Vollhardt, K. P. C. J. Mol. Catal. 1990, 60, 323.
    • 3/Aliquat 336 catalyst: Amer, L.; Blum, J.; Vollhardt, K. P. C. J. Mol. Catal. 1990, 60, 323.
  • 139
    • 47249092689 scopus 로고    scopus 로고
    • Saito, S.; Yamamoto, Y. Palladium-Catalyzed Benzannulation Reactions of Conjugated Enynes and Diynes. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002.
    • (b) Saito, S.; Yamamoto, Y. Palladium-Catalyzed Benzannulation Reactions of Conjugated Enynes and Diynes. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002.
  • 143
    • 33846689405 scopus 로고    scopus 로고
    • (a) Nolan, S. P. Nature 2007, 445, 496.
    • (2007) Nature , vol.445 , pp. 496
    • Nolan, S.P.1
  • 146


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.