Unknown

Dataset Information

0

Substitution of fluorine in M[C6F5BF3] with organolithium compounds: distinctions between O- and N-nucleophiles.


ABSTRACT: Borates M[C6F5BF3] (M = K, Li, Bu4N) react with organolithium compounds, RLi (R = Me, Bu, Ph), in 1,2-dimethoxyethane or diglyme to give M[4-RC6F4BF3] and M[2-RC6F4BF3]. When R is Me or Bu, the nucleophilic substitution of the fluorine atom at the para position to boron is the predominant route. When R = Ph, the ratio M[4-RC6F4BF3]/M[2-RC6F4BF3] is ca. 1:1. Substitution of the fluorine atom at the ortho position to boron is solely caused by the coordination of RLi via the lithium atom with the fluorine atoms of the BF3 group. This differs from the previously reported substitution in K[C6F5BF3] by O- and N-nucleophiles that did not produce K[2-NuC6F4BF3].

SUBMITTER: Shabalin AY 

PROVIDER: S-EPMC5405681 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

altmetric image

Publications

Substitution of fluorine in M[C<sub>6</sub>F<sub>5</sub>BF<sub>3</sub>] with organolithium compounds: distinctions between O- and N-nucleophiles.

Shabalin Anton Yu AY   Adonin Nicolay Yu NY   Bardin Vadim V VV  

Beilstein journal of organic chemistry 20170412


Borates M[C<sub>6</sub>F<sub>5</sub>BF<sub>3</sub>] (M = K, Li, Bu<sub>4</sub>N) react with organolithium compounds, RLi (R = Me, Bu, Ph), in 1,2-dimethoxyethane or diglyme to give M[4-RC<sub>6</sub>F<sub>4</sub>BF<sub>3</sub>] and M[2-RC<sub>6</sub>F<sub>4</sub>BF<sub>3</sub>]. When R is Me or Bu, the nucleophilic substitution of the fluorine atom at the <i>para</i> position to boron is the predominant route. When R = Ph, the ratio M[4-RC<sub>6</sub>F<sub>4</sub>BF<sub>3</sub>]/M[2-RC<sub>6</su  ...[more]

Similar Datasets

| S-EPMC8233348 | biostudies-literature
2017-03-03 | GSE90104 | GEO
| S-EPMC8609525 | biostudies-literature
| S-EPMC4748252 | biostudies-literature
| S-EPMC6005182 | biostudies-literature
| S-EPMC6002767 | biostudies-literature
| S-EPMC4895725 | biostudies-literature
| S-EPMC3241867 | biostudies-literature
| S-EPMC3458738 | biostudies-literature
| S-EPMC6916363 | biostudies-literature