Reactions of zinc dialkyls with (perfluorophenyl)boron compounds: Alkylzinc cation formation vs C6F5 transfer

Dennis A. Walker; Timothy J. Woodman; David L. Hughes; Manfred Bochmann

doi:10.1021/om0103557

Reactions of zinc dialkyls with (perfluorophenyl)boron compounds: Alkylzinc cation formation vs C₆F₅ transfer

Dennis A. Walker, Timothy J. Woodman, David L. Hughes, Manfred Bochmann

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

100 Citations (Scopus)

Abstract

Reaction between ZnR₂ and [H(OEt₂)₂][B(C₆F₅)₄] in ether leads to the salts [RZn(OEt₂)₃][B(C₆F₅)₄], while mixtures of ZnR₂ (R = Me, Et) and B(C₆F₅)₃ in toluene-d₈ undergo facile alkyl/C₆F₅ group exchange to give Zn(C₆F₅)₂·(toluene). Mixtures of ZnR₂ and B(C₆F₅)₃ in hydrocarbon/diethyl ether solvent mixtures react with alkyl transfer to afford the ion pairs [RZn(OEt₂)₃][RB(C₆F₅)₃], whereas the reaction of ZnEt₂ with [Ph₃C][B(C₆F₅)₄] in toluene-d₈ proceeds with ß-H abstraction to give ethene and Ph₃CH, with the subsequent rapid formation of Zn(C₆F₅)₂.

Original language	English
Pages (from-to)	3772-3776
Number of pages	5
Journal	Organometallics
Volume	20
Issue number	17
DOIs	https://doi.org/10.1021/om0103557
Publication status	Published - 20 Jul 2001

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@article{a4bfb690df9a45c39618737ac3e7ac32,

title = "Reactions of zinc dialkyls with (perfluorophenyl)boron compounds: Alkylzinc cation formation vs C6F5 transfer",

abstract = "Reaction between ZnR2 and [H(OEt2)2][B(C6F5)4] in ether leads to the salts [RZn(OEt2)3][B(C6F5)4], while mixtures of ZnR2 (R = Me, Et) and B(C6F5)3 in toluene-d8 undergo facile alkyl/C6F5 group exchange to give Zn(C6F5)2·(toluene). Mixtures of ZnR2 and B(C6F5)3 in hydrocarbon/diethyl ether solvent mixtures react with alkyl transfer to afford the ion pairs [RZn(OEt2)3][RB(C6F5)3], whereas the reaction of ZnEt2 with [Ph3C][B(C6F5)4] in toluene-d8 proceeds with {\ss}-H abstraction to give ethene and Ph3CH, with the subsequent rapid formation of Zn(C6F5)2.",

author = "Walker, {Dennis A.} and Woodman, {Timothy J.} and Hughes, {David L.} and Manfred Bochmann",

year = "2001",

month = jul,

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doi = "10.1021/om0103557",

language = "English",

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pages = "3772--3776",

journal = "Organometallics",

issn = "1520-6041",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Reactions of zinc dialkyls with (perfluorophenyl)boron compounds: Alkylzinc cation formation vs C6F5 transfer

AU - Walker, Dennis A.

AU - Woodman, Timothy J.

AU - Hughes, David L.

AU - Bochmann, Manfred

PY - 2001/7/20

Y1 - 2001/7/20

N2 - Reaction between ZnR2 and [H(OEt2)2][B(C6F5)4] in ether leads to the salts [RZn(OEt2)3][B(C6F5)4], while mixtures of ZnR2 (R = Me, Et) and B(C6F5)3 in toluene-d8 undergo facile alkyl/C6F5 group exchange to give Zn(C6F5)2·(toluene). Mixtures of ZnR2 and B(C6F5)3 in hydrocarbon/diethyl ether solvent mixtures react with alkyl transfer to afford the ion pairs [RZn(OEt2)3][RB(C6F5)3], whereas the reaction of ZnEt2 with [Ph3C][B(C6F5)4] in toluene-d8 proceeds with ß-H abstraction to give ethene and Ph3CH, with the subsequent rapid formation of Zn(C6F5)2.

AB - Reaction between ZnR2 and [H(OEt2)2][B(C6F5)4] in ether leads to the salts [RZn(OEt2)3][B(C6F5)4], while mixtures of ZnR2 (R = Me, Et) and B(C6F5)3 in toluene-d8 undergo facile alkyl/C6F5 group exchange to give Zn(C6F5)2·(toluene). Mixtures of ZnR2 and B(C6F5)3 in hydrocarbon/diethyl ether solvent mixtures react with alkyl transfer to afford the ion pairs [RZn(OEt2)3][RB(C6F5)3], whereas the reaction of ZnEt2 with [Ph3C][B(C6F5)4] in toluene-d8 proceeds with ß-H abstraction to give ethene and Ph3CH, with the subsequent rapid formation of Zn(C6F5)2.

U2 - 10.1021/om0103557

DO - 10.1021/om0103557

M3 - Article

SN - 1520-6041

VL - 20

SP - 3772

EP - 3776

JO - Organometallics

JF - Organometallics

IS - 17

ER -