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Volumn 69, Issue 25, 2004, Pages 8574-8582

From dimerization, to cycloaddition, to atom transfer cyclization: The further chemistry of TMM diradicals

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CHEMICAL REACTIONS; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; TRANSPORT PROPERTIES;

EID: 10044219812     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048717i     Document Type: Article
Times cited : (14)

References (29)
  • 2
    • 10044222995 scopus 로고
    • Borden, W. T., Ed.; Wiley: New York; Chapter 4
    • (b) Berson, J. A. In Diradicals; Borden, W. T., Ed.; Wiley: New York, 1982; Chapter 4.
    • (1982) Diradicals
    • Berson, J.A.1
  • 4
    • 0002036283 scopus 로고    scopus 로고
    • Atom transfer reactions
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: New York, Chapter 1.5
    • (b) Byers, J. Atom Transfer Reactions. In Radicals In Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: New York, 2001; Vol. 1, Chapter 1.5.
    • (2001) Radicals in Organic Synthesis , vol.1
    • Byers, J.1
  • 5
    • 0001238367 scopus 로고    scopus 로고
    • Hydrogen atom abstraction
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: New York, Chapter 3.6
    • (c) Feray, L.; Kuznetsov, N.; Renaud, P. Hydrogen Atom Abstraction. In Radicals In Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: New York, 2001; Vol. 1, Chapter 3.6.
    • (2001) Radicals in Organic Synthesis , vol.1
    • Feray, L.1    Kuznetsov, N.2    Renaud, P.3
  • 8
    • 0002658567 scopus 로고    scopus 로고
    • (b) Tittle, R. D. Chem. Rev. 1996, 96 (1), 93.
    • (1996) Chem. Rev. , vol.96 , Issue.1 , pp. 93
    • Tittle, R.D.1
  • 9
    • 10044270596 scopus 로고    scopus 로고
    • note
    • (a) A reviewer has offered a reasonable alternative explanation. The rationale posits that a reversible cyclization of 24 would lead to an unstabilized oxygen-centered radical that would quickly revert to 24. In contrast, both the cyclization of 27 and 29 would afford a stabilized radical. Perhaps, as the reviewer suggested, stabilization increases the lifetime of the intermediate enough to allow formation of the second σ-bond to occur.
  • 11
    • 10044274996 scopus 로고    scopus 로고
    • note
    • The transformations appearing in this paper represent the first reported examples of the use of Lewis acids in conjunction with TMM diyl chemistry.
  • 17
    • 10044278927 scopus 로고    scopus 로고
    • note
    • (a) Calculations were conducted with the Spartan 02 PC Software program available from Wavefunction, Inc.
  • 18
    • 10044248046 scopus 로고    scopus 로고
    • note
    • (b) Monoradicals and TMM diyls differ in several important ways. In particular, the latter can exist in more than one spin state (singlet/triplet) whose geometries (planar/bisected) and chemistries often differ, and second, because they are diradicals, there are two possible sites to which atom transfer can occur. That a 1,7-hydrogen transfer is not observed despite the fact that the transition state for it is calculated to reside only 1 kcal/mol above that for the 1,5 transfer is consistent with the notion that such a process is slowed entropically by the necessity to form an eight-membered ring in the transition structure leading to transfer.
  • 21
    • 0001646991 scopus 로고    scopus 로고
    • Calculations: A useful tool for synthetic chemists
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: New York, Chapter 3.2 and references therein
    • (c) Schliesser, C. H.; Skidmore, M. A. Calculations: a Useful Tool for Synthetic Chemists. In Radicals In Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: New York, 2001; Vol. 1, Chapter 3.2 and references therein.
    • (2001) Radicals in Organic Synthesis , vol.1
    • Schliesser, C.H.1    Skidmore, M.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.