Nucleophilic addition and displacement in the reaction of 2,4,6-trimethylphenoxide ion with 1,3,5-trinitrobenzene. An oxygen-bonded aryloxide σ-complex
Тип публикации: Journal Article
Дата публикации: 1981-08-15
SCImago Q3
WOS Q4
БС3
SJR: 0.28
CiteScore: 2.1
Impact factor: 1
ISSN: 00084042, 14803291
General Chemistry
Catalysis
Organic Chemistry
Краткое описание
Reaction of 1,3,5-trinitrobenzene with potassium 2,4,6-trimethylphenoxide in dimethyl sulfoxide solution leads to σ-complex formation concurrently with displacement of a nitro group. The results provide definitive evidence for σ-complex formation via the oxygen of aryloxide ion in this system, and contrast with the situation that obtains with phenoxide ion itself, which under corresponding conditions yields the carbon-bonded σ-complex as the product of thermodynamic control. Stereoelectronic factors in σ -complex formation and in the diaryl ether resulting from nitro displacement are also discussed.
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Buncel E. et al. Nucleophilic addition and displacement in the reaction of 2,4,6-trimethylphenoxide ion with 1,3,5-trinitrobenzene. An oxygen-bonded aryloxide σ-complex // Canadian Journal of Chemistry. 1981. Vol. 59. No. 16. pp. 2470-2474.
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Buncel E., Moir R. Y., Norris A. R., Chatrousse A. Nucleophilic addition and displacement in the reaction of 2,4,6-trimethylphenoxide ion with 1,3,5-trinitrobenzene. An oxygen-bonded aryloxide σ-complex // Canadian Journal of Chemistry. 1981. Vol. 59. No. 16. pp. 2470-2474.
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TY - JOUR
DO - 10.1139/v81-356
UR - https://doi.org/10.1139/v81-356
TI - Nucleophilic addition and displacement in the reaction of 2,4,6-trimethylphenoxide ion with 1,3,5-trinitrobenzene. An oxygen-bonded aryloxide σ-complex
T2 - Canadian Journal of Chemistry
AU - Buncel, Erwin
AU - Moir, Robert Y.
AU - Norris, Albert R.
AU - Chatrousse, Alain-Pierre
PY - 1981
DA - 1981/08/15
PB - Canadian Science Publishing
SP - 2470-2474
IS - 16
VL - 59
SN - 0008-4042
SN - 1480-3291
ER -
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@article{1981_Buncel,
author = {Erwin Buncel and Robert Y. Moir and Albert R. Norris and Alain-Pierre Chatrousse},
title = {Nucleophilic addition and displacement in the reaction of 2,4,6-trimethylphenoxide ion with 1,3,5-trinitrobenzene. An oxygen-bonded aryloxide σ-complex},
journal = {Canadian Journal of Chemistry},
year = {1981},
volume = {59},
publisher = {Canadian Science Publishing},
month = {aug},
url = {https://doi.org/10.1139/v81-356},
number = {16},
pages = {2470--2474},
doi = {10.1139/v81-356}
}
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Buncel, Erwin, et al. “Nucleophilic addition and displacement in the reaction of 2,4,6-trimethylphenoxide ion with 1,3,5-trinitrobenzene. An oxygen-bonded aryloxide σ-complex.” Canadian Journal of Chemistry, vol. 59, no. 16, Aug. 1981, pp. 2470-2474. https://doi.org/10.1139/v81-356.
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