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Volumn , Issue 19, 2006, Pages 4528-4536

Photochemical electron-transfer generation of arylthiirane radical cations with tetranitromethane and chloranil - Some novel observations

Author keywords

Nitration oxidative cleavage; Photochemistry; Photoinduced electron transfer; Radicals; Thiirane

Indexed keywords


EID: 33749439143     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600400     Document Type: Article
Times cited : (7)

References (55)
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    • (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford
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    • (1996) Comprehensive Heterocyclic Chemistry II , vol.1 A , pp. 173-240
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    • (Ed.: E. D. Lwowski), Pergamon, Oxford
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    • note
    • [7]
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    • note
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    • note
    • [17b]
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    • 33749436634 scopus 로고    scopus 로고
    • note
    • For the arylthiirane radical cations, the β-fragmentation of the intermediate thiyl radical is favored over the dimerization reaction which, is the main pathway with alkylthiiranes [Equation (1)]. This different behavior is probably due to the C-C bond dissociation energy, which is lower in the arylthiirane than in the alkylthiirane radical cations.
  • 47
    • 33749439229 scopus 로고    scopus 로고
    • note
    • 4 can be also ascribed to the nucleophilic attack of water on the distonic radical cation 15.
  • 50
    • 33749441075 scopus 로고    scopus 로고
    • note
    • b) Semiempirical calculations were performed with the AM1/UHF method, as implemented in the AMPAC package from the Quantum Chemistry Program Exchange (QCPE), program no. 506.
  • 52
    • 33749435672 scopus 로고    scopus 로고
    • note
    • In the alkylthiirane radical cations, the spin density should also be located on the sulfur atom. Nevertheless, these species do not afford the alkene [Equation (1)], probably due to the higher enthalpy change in the formation of the alkene radical cations.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.