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Eliminations from (E)-2,4-Dinitrobenzaldehyde O-Aryloximes Promoted by R3N in MeCN. Effects of beta-Aryl Group and Base-Solvent on the Nitrile-Forming Transition-State
- Authors
- Cho, Bong Rae; Ryu, Eun Mi; Pyun, Sang Yong
- Issue Date
- 20-9월-2012
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- Elimination; E2 and E1cb-like
- Citation
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.33, no.9, pp.2976 - 2980
- Indexed
- SCIE
SCOPUS
KCI
- Journal Title
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY
- Volume
- 33
- Number
- 9
- Start Page
- 2976
- End Page
- 2980
- ISSN
- 0253-2964
- Abstract
- Nitrile-forming eliminations from (E)-2,4-(NO2)(2)C6H2CH=NOC6H4-2-X-4-NO2 (1a-e) promoted by R3N in MeCN have been studied kinetically. The reactions are second-order and exhibit Bronsted beta = 0.83-1.0 and vertical bar beta(1g)vertical bar = 0.41-0.46. The results have been interpreted in terms of highly E1cb-like transition state with extensive C-beta-H bond cleavage and limited N-alpha-OAr bond cleavage. Comparison with existing data reveals that the structure of the transition state changes from E2-central to highly E1cb-like either by the change of the beta-aryl group from Ph to 2,4-dinitrophenyl under the same condition or by the base-solvent system variation from EtO--EtOH to Et3N-MeCN for a given substrate (1a-e).
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