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Volumn 11, Issue 21, 2005, Pages 6175-6184

Preparation and reactivity of [D3d]-octahedrane: The most stable (CH)12 hydrocarbon

Author keywords

Density functional calculations; Halogenation, heats of formation; Phase transfer catalysis; Polycycles; Small rings

Indexed keywords

HYDROGEN BONDS; HYDROGENATION; MOLECULAR STRUCTURE; PHASE TRANSITIONS; REACTION KINETICS; STRAIN CONTROL; SYNTHESIS (CHEMICAL);

EID: 27344443123     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500472     Document Type: Article
Times cited : (27)

References (59)
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    • b) G. J. Lees, DRUGS 2000, 59, 33-78.
    • (2000) DRUGS , vol.59 , pp. 33-78
    • Lees, G.J.1
  • 5
    • 0004189662 scopus 로고
    • (Ed.: G. A. Olah), Wiley, New York
    • a) P. v. R. Schleyer, in Cage Hydrocarbons (Ed.: G. A. Olah), Wiley, New York, 1990, pp. 1-38;
    • (1990) Cage Hydrocarbons , pp. 1-38
    • Schleyer, P.V.R.1
  • 8
    • 27344434569 scopus 로고    scopus 로고
    • note
    • -1at B3LYP/ 6-311+G** in favor of 1).
  • 31
    • 0035825188 scopus 로고    scopus 로고
    • and references therein
    • Angew. Chem. Int. Ed. 2001, 40, 180-183, and references therein.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 180-183
  • 32
    • 27344446847 scopus 로고    scopus 로고
    • note
    • 9decane], may undergo rearrangement in contact with platinum(0) prior to hydrogenolytic ring opening, compare ref. [25].
  • 34
    • 27344451406 scopus 로고
    • and references therein
    • Angew. Chem. Int. Ed. Engl. 1983, 22, 1-12, and references therein.
    • (1983) Angew. Chem. Int. Ed. Engl. , vol.22 , pp. 1-12
  • 45
    • 27344451710 scopus 로고    scopus 로고
    • note
    • The 1- and 2-octahedryl cations have virtually the same energy at B3LYP/6-31G*.
  • 46
    • 0037063515 scopus 로고    scopus 로고
    • Recent studies on the mechanisms of alkane functionalizations with oxidizing electrophiles (A. A. Fokin, T. E. Shubina, P. A. Gunchen ko, S. D. Isaev, A. G. Yurchenko, P. R. Schreiner, J. Am. Chem. Soc. 2002, 124, 10718-10727) revealed that the transition structures are characterized by significant charge transfer to the electrophile, and the hydrocarbon moieties resemble the respective radical cation structures (H-coupled electron transfer). Compound 1 forms a radical cation with one elongated C-C bond (1.855 Å, B3LYP/6-31G*) in the cyclopropane moiety showing that the most favorable reaction path with electrophilic reagents involves C-C bond breaking.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10718-10727
    • Fokin, A.A.1    Shubina, T.E.2    Ko, P.A.G.3    Isaev, S.D.4    Yurchenko, A.G.5    Schreiner, P.R.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.