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Volumn 74, Issue 6, 2009, Pages 2601-2604

Facile synthesis of β-tribromomethyl and dibromomethylenated nitroalkanes via conjugate addition of bromoform to nitroalkenes

Author keywords

[No Author keywords available]

Indexed keywords

BROMOFORM; CONJUGATE ADDITIONS; DIASTEREO SELECTIVITIES; DIBROMIDES; FACILE SYNTHESIS; GOOD YIELDS; MICHAEL-ADDUCTS; NITROALKANES; NITROALKENES; ONE POTS;

EID: 64149099330     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802274q     Document Type: Article
Times cited : (19)

References (44)
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    • +) in ca. 1:3:3:1 ratio in the mass spectrum.
    • +) in ca. 1:3:3:1 ratio in the mass spectrum.
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    • 1H COSY experiment. NOE is also observed between the two vicinal protons. The structure was further unambiguously established by single crystal X-ray analysis (see the Supporting Information).
    • 1H COSY experiment. NOE is also observed between the two vicinal protons. The structure was further unambiguously established by single crystal X-ray analysis (see the Supporting Information).
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    • 2 (see the Supporting Information).
    • 2 (see the Supporting Information).
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    • +) in ca. 1:2:1 ratio in the mass spectrum.
    • +) in ca. 1:2:1 ratio in the mass spectrum.
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    • In bromoform a carbon-halogen bond is broken in the initiation step: Weizmann, M.; Israelashvili, S.; Halevv, A.; Bergmann, F. J. Am. Chem. Soc. 1947, 69, 2569.
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    • The absence of benzene may be due to the inability of the highly resonance stabilized nitroalkyl radical to abstract H radical from 1,4-cyclohexadiene (the product 2a could be formed during aqueous workup) or polymerization rather than aromatization of the 1,4-cyclohexadienyl radical.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.