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Preparation of heptafluoronaphthyllithiums and -magnesiums : An unexpected difference in the reactivity of isomers C10F7H and C10F7Br towards organolithium and organomagnesium compounds. / Shmakov, Mikhail M.; Bardin, Vadim V.; Prikhod'ko, Sergey A. et al.

In: Journal of Organometallic Chemistry, Vol. 899, 120889, 30.10.2019.

Research output: Contribution to journal › Article › peer-review

Harvard

Shmakov, MM, Bardin, VV, Prikhod'ko, SA & Adonin, NY 2019, 'Preparation of heptafluoronaphthyllithiums and -magnesiums: An unexpected difference in the reactivity of isomers C10F7H and C10F7Br towards organolithium and organomagnesium compounds', Journal of Organometallic Chemistry, vol. 899, 120889. https://doi.org/10.1016/j.jorganchem.2019.120889

APA

Shmakov, M. M., Bardin, V. V., Prikhod'ko, S. A., & Adonin, N. Y. (2019). Preparation of heptafluoronaphthyllithiums and -magnesiums: An unexpected difference in the reactivity of isomers C10F7H and C10F7Br towards organolithium and organomagnesium compounds. Journal of Organometallic Chemistry, 899, [120889]. https://doi.org/10.1016/j.jorganchem.2019.120889

Vancouver

Shmakov MM, Bardin VV, Prikhod'ko SA, Adonin NY. Preparation of heptafluoronaphthyllithiums and -magnesiums: An unexpected difference in the reactivity of isomers C10F7H and C10F7Br towards organolithium and organomagnesium compounds. Journal of Organometallic Chemistry. 2019 Oct 30;899:120889. doi: 10.1016/j.jorganchem.2019.120889

Author

Shmakov, Mikhail M. ; Bardin, Vadim V. ; Prikhod'ko, Sergey A. et al. / Preparation of heptafluoronaphthyllithiums and -magnesiums : An unexpected difference in the reactivity of isomers C10F7H and C10F7Br towards organolithium and organomagnesium compounds. In: Journal of Organometallic Chemistry. 2019 ; Vol. 899.

BibTeX

@article{c1bb6b86e50f4c9db13db2102a6e23f5,
title = "Preparation of heptafluoronaphthyllithiums and -magnesiums: An unexpected difference in the reactivity of isomers C10F7H and C10F7Br towards organolithium and organomagnesium compounds",
abstract = "Significant differences in the reactivity of isomeric heptafluoronaphthalenes and bromoheptafluoronaphthalenes towards organolithium and organomagnesium compounds were found. Metalation of polyfluorinated naphthalenes 2-C10F7X (X = H, Br) occurs easily under the action of bases (BuLi, t-BuLi, LDA) as well as EtMgBr (X = Br) in ether. This fact was proven by 19F NMR spectroscopy and by trapping of 2-C10F7M (M = Li, MgBr, Mg(2-C10F7)) with electrophile ClSiMe3. The interaction of 1-C10F7Br with BuLi or EtMgBr proceeds in a similar way. In contrast to 2-C10F7H, isomeric 1-C10F7H is the less acidic substrate and undergoes only the nucleophilic alkyldefluorination when combined with BuLi or t-BuLi.",
keywords = "Alkyllithium, Bromoheptafluoronaphthalene, Ethylmagnesium bromide, Heptafluoronaphthalene, Metalation, Trimethylsilylheptafluoronaphthalene, REAGENTS",
author = "Shmakov, {Mikhail M.} and Bardin, {Vadim V.} and Prikhod'ko, {Sergey A.} and Adonin, {Nicolay Yu}",
note = "Publisher Copyright: {\textcopyright} 2019",
year = "2019",
month = oct,
day = "30",
doi = "10.1016/j.jorganchem.2019.120889",
language = "English",
volume = "899",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Preparation of heptafluoronaphthyllithiums and -magnesiums

T2 - An unexpected difference in the reactivity of isomers C10F7H and C10F7Br towards organolithium and organomagnesium compounds

AU - Shmakov, Mikhail M.

AU - Bardin, Vadim V.

AU - Prikhod'ko, Sergey A.

AU - Adonin, Nicolay Yu

N1 - Publisher Copyright: © 2019

PY - 2019/10/30

Y1 - 2019/10/30

N2 - Significant differences in the reactivity of isomeric heptafluoronaphthalenes and bromoheptafluoronaphthalenes towards organolithium and organomagnesium compounds were found. Metalation of polyfluorinated naphthalenes 2-C10F7X (X = H, Br) occurs easily under the action of bases (BuLi, t-BuLi, LDA) as well as EtMgBr (X = Br) in ether. This fact was proven by 19F NMR spectroscopy and by trapping of 2-C10F7M (M = Li, MgBr, Mg(2-C10F7)) with electrophile ClSiMe3. The interaction of 1-C10F7Br with BuLi or EtMgBr proceeds in a similar way. In contrast to 2-C10F7H, isomeric 1-C10F7H is the less acidic substrate and undergoes only the nucleophilic alkyldefluorination when combined with BuLi or t-BuLi.

AB - Significant differences in the reactivity of isomeric heptafluoronaphthalenes and bromoheptafluoronaphthalenes towards organolithium and organomagnesium compounds were found. Metalation of polyfluorinated naphthalenes 2-C10F7X (X = H, Br) occurs easily under the action of bases (BuLi, t-BuLi, LDA) as well as EtMgBr (X = Br) in ether. This fact was proven by 19F NMR spectroscopy and by trapping of 2-C10F7M (M = Li, MgBr, Mg(2-C10F7)) with electrophile ClSiMe3. The interaction of 1-C10F7Br with BuLi or EtMgBr proceeds in a similar way. In contrast to 2-C10F7H, isomeric 1-C10F7H is the less acidic substrate and undergoes only the nucleophilic alkyldefluorination when combined with BuLi or t-BuLi.

KW - Alkyllithium

KW - Bromoheptafluoronaphthalene

KW - Ethylmagnesium bromide

KW - Heptafluoronaphthalene

KW - Metalation

KW - Trimethylsilylheptafluoronaphthalene

KW - REAGENTS

UR - http://www.scopus.com/inward/record.url?scp=85070596364&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2019.120889

DO - 10.1016/j.jorganchem.2019.120889

M3 - Article

AN - SCOPUS:85070596364

VL - 899

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

M1 - 120889

ER -

ID: 21254546