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Volumn 133, Issue 8, 2011, Pages 2424-2426

Expeditious construction of a carbobicyclic skeleton via sp3-C-H functionalization: Hydride shift from an aliphatic tertiary position in an internal redox process

Author keywords

[No Author keywords available]

Indexed keywords

C-H FUNCTIONALIZATION; FIVE-MEMBERED RINGS; REDOX PROCESS;

EID: 79952271674     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja110520p     Document Type: Article
Times cited : (141)

References (57)
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    • These types of reactions have been classified under the term tert -amino effect. For reviews, see: Meth-Cohn, O.; Suschitzky, H. Adv. Heterocycl. Chem. 1972, 14, 211
    • (1972) Adv. Heterocycl. Chem. , vol.14 , pp. 211
    • Meth-Cohn, O.1    Suschitzky, H.2
  • 42
    • 67649342031 scopus 로고    scopus 로고
    • For another benzylic hydride shift/ring closure for the formation of tetraline derivatives, see: Mahoney, S. J.; Moon, D. T.; Hollinger, J.; Fillion, E. Tetrahedron Lett. 2009, 50, 4706
    • (2009) Tetrahedron Lett. , vol.50 , pp. 4706
  • 43
    • 33746905548 scopus 로고    scopus 로고
    • For hydride shifts from di- and/or triarylmethane, see: Bajracharya, G. B.; Pahadi, N. K.; Gridnev, I. D.; Yamamoto, Y. J. Org. Chem. 2006, 71, 6204
    • (2006) J. Org. Chem. , vol.71 , pp. 6204
  • 51
    • 79952254325 scopus 로고    scopus 로고
    • 3, see refs 2a, 2j, 4j, 4m, 6, and 7c.
    • 3, see refs 2a, 2j, 4j, 4m, 6, and 7c.
  • 52
    • 79952268622 scopus 로고    scopus 로고
    • In order to obtain information about the reaction course, some D-labeling experiments were conducted. The results are described in the Supporting Information.
    • In order to obtain information about the reaction course, some D-labeling experiments were conducted. The results are described in the Supporting Information.
  • 53
    • 79952273324 scopus 로고
    • For a theoretical study of the effect of the substituent on the stability of a carbocation, see: El-Nahas, A. M.; Clark, T. J. Org. Chem. 1995, 60, 6024
    • (1995) J. Org. Chem. , vol.60 , pp. 6024
    • El-Nahas, A.M.1    Clark, T.2
  • 54
    • 79952258500 scopus 로고    scopus 로고
    • We assumed that there are two factors contributing to the predominant formation of a five-membered ring over a seven-membered ring: (1) Baldwin's rule and (2) steric repulsion between the bulky barbituric acid moiety and the dimethyl group around the tertiary carbocation in the transition state for the formation of a seven-membered ring.
    • We assumed that there are two factors contributing to the predominant formation of a five-membered ring over a seven-membered ring: (1) Baldwin's rule and (2) steric repulsion between the bulky barbituric acid moiety and the dimethyl group around the tertiary carbocation in the transition state for the formation of a seven-membered ring.
  • 55
    • 79952271406 scopus 로고    scopus 로고
    • Zhou and Zhang reported a gold-catalyzed internal redox reaction involving C-C bond formation between a furanyl anion species and a carbocation generated by the hydride shift (see ref 2j).
    • Zhou and Zhang reported a gold-catalyzed internal redox reaction involving C-C bond formation between a furanyl anion species and a carbocation generated by the hydride shift (see ref 2j).
  • 56
    • 79952269910 scopus 로고    scopus 로고
    • 2Cl (1.0 mL) at refluxing temperature.
    • 2Cl (1.0 mL) at refluxing temperature.
  • 57
    • 79952268235 scopus 로고    scopus 로고
    • One of the reviewers suggested the intermolecular hydride shift mechanism. The crossover experiment of d - 3g and a naphthyl-type substrate revealed that the hydride shift occurred intramolecularly. For more detailed information, see the Supporting Information. We thank the reviewer for the suggestion of this experiment.
    • One of the reviewers suggested the intermolecular hydride shift mechanism. The crossover experiment of d-3g and a naphthyl-type substrate revealed that the hydride shift occurred intramolecularly. For more detailed information, see the Supporting Information. We thank the reviewer for the suggestion of this experiment.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.