Effect of Solvent on the Lithium−Bromine Exchange of Aryl Bromides: Reactions of n-Butyllithium and tert-Butyllithium with 1-Bromo-4-tert-butylbenzene at 0 °C
Publication type: Journal Article
Publication date: 2006-03-01
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
16555838
Organic Chemistry
Abstract
The outcome of reactions of 1-bromo-4-tert-butylbenzene (1), a representative aryl bromide, with n-BuLi or t-BuLi at 0 °C in a variety of solvent systems has been investigated. The products of reactions of 1 with n-BuLi vary significantly with changes in solvent composition: 1 does not react with n-BuLi in pure heptane; the exchange reaction to give (4-tert-butylphenyl)lithium, which is slow in pure diethyl ether, is virtually quantitative in heptane containing a small quantity of THF; and the reaction of 1 with n-BuLi in THF leads to considerable coupling. Lithium−bromine exchange is the virtually exclusive outcome of reactions of 1 with t-BuLi in every solvent studied except pure heptane: the presence of a small quantity of any of a variety of structurally diverse ethers (Et2O, THF, THP, MTBE) in the predominantly hydrocarbon medium affords (4-tert-butylphenyl)lithium, assayed as tert-butylbenzene, in yields exceeding 97%. The only side products observed from reactions of 1 with t-BuLi are small amounts of benzyne-derived hydrocarbons.
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54
Total citations:
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Citations from 2024:
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(5.55%)
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GOST
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Bailey W. F., Luderer M. R., Jordan K. P. Effect of Solvent on the Lithium−Bromine Exchange of Aryl Bromides: Reactions of n-Butyllithium and tert-Butyllithium with 1-Bromo-4-tert-butylbenzene at 0 °C // Journal of Organic Chemistry. 2006. Vol. 71. No. 7. pp. 2825-2828.
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Bailey W. F., Luderer M. R., Jordan K. P. Effect of Solvent on the Lithium−Bromine Exchange of Aryl Bromides: Reactions of n-Butyllithium and tert-Butyllithium with 1-Bromo-4-tert-butylbenzene at 0 °C // Journal of Organic Chemistry. 2006. Vol. 71. No. 7. pp. 2825-2828.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo060026u
UR - https://doi.org/10.1021/jo060026u
TI - Effect of Solvent on the Lithium−Bromine Exchange of Aryl Bromides: Reactions of n-Butyllithium and tert-Butyllithium with 1-Bromo-4-tert-butylbenzene at 0 °C
T2 - Journal of Organic Chemistry
AU - Bailey, William F.
AU - Luderer, Mark R
AU - Jordan, Kevin P.
PY - 2006
DA - 2006/03/01
PB - American Chemical Society (ACS)
SP - 2825-2828
IS - 7
VL - 71
PMID - 16555838
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2006_Bailey,
author = {William F. Bailey and Mark R Luderer and Kevin P. Jordan},
title = {Effect of Solvent on the Lithium−Bromine Exchange of Aryl Bromides: Reactions of n-Butyllithium and tert-Butyllithium with 1-Bromo-4-tert-butylbenzene at 0 °C},
journal = {Journal of Organic Chemistry},
year = {2006},
volume = {71},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/jo060026u},
number = {7},
pages = {2825--2828},
doi = {10.1021/jo060026u}
}
Cite this
MLA
Copy
Bailey, William F., et al. “Effect of Solvent on the Lithium−Bromine Exchange of Aryl Bromides: Reactions of n-Butyllithium and tert-Butyllithium with 1-Bromo-4-tert-butylbenzene at 0 °C.” Journal of Organic Chemistry, vol. 71, no. 7, Mar. 2006, pp. 2825-2828. https://doi.org/10.1021/jo060026u.