Aluminyl derived ethene functionalization with heteroallenes, leading to an intramolecular ligand rearrangement

Andrea O'Reilly; Michael G. Gardiner; Claire L. McMullin; J. Robin Fulton; Martyn P. Coles

doi:10.1039/D3CC05785B

Aluminyl derived ethene functionalization with heteroallenes, leading to an intramolecular ligand rearrangement

Andrea O'Reilly, Michael G. Gardiner, Claire L. McMullin, J. Robin Fulton, Martyn P. Coles

Department of Chemistry

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2 Citations (SciVal)

Abstract

The aluminacyclopropane K[Al(NON)(η-C ₂H ₄)] ([NON] ²⁻ = [O(SiMe ₂NDipp) ₂] ²⁻, Dipp = 2,6-iPr ₂C ₆H ₃) reacts with CO ₂ and iPrN 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 C NiPr to afford ring-expanded products of C-C bond formation. The latter system undergoes a 1,3-silyl retro-Brook rearrangement of the NON-group, to afford the [NNO] ²⁻ ligand ([NNO] ²⁻ = [N(Dipp)SiMe ₂N(Dipp)SiMe ₂O] ²⁻). The mechanism of transformation was examined by density functional theory (DFT).

Original language	English
Pages (from-to)	881-884
Number of pages	4
Journal	Chemical Communications
Volume	60
Issue number	7
Early online date	22 Dec 2023
DOIs	https://doi.org/10.1039/D3CC05785B
Publication status	Published - 21 Jan 2024

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10.1039/D3CC05785BLicence: CC BY

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title = "Aluminyl derived ethene functionalization with heteroallenes, leading to an intramolecular ligand rearrangement",

abstract = "The aluminacyclopropane K[Al(NON)(η-C 2H 4)] ([NON] 2− = [O(SiMe 2NDipp) 2] 2−, Dipp = 2,6-iPr 2C 6H 3) reacts with CO 2 and iPrN 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 C NiPr to afford ring-expanded products of C-C bond formation. The latter system undergoes a 1,3-silyl retro-Brook rearrangement of the NON-group, to afford the [NNO] 2− ligand ([NNO] 2− = [N(Dipp)SiMe 2N(Dipp)SiMe 2O] 2−). The mechanism of transformation was examined by density functional theory (DFT).",

author = "Andrea O'Reilly and Gardiner, {Michael G.} and McMullin, {Claire L.} and Fulton, {J. Robin} and Coles, {Martyn P.}",

year = "2024",

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day = "21",

doi = "10.1039/D3CC05785B",

language = "English",

volume = "60",

pages = "881--884",

journal = "Chemical Communications",

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TY - JOUR

T1 - Aluminyl derived ethene functionalization with heteroallenes, leading to an intramolecular ligand rearrangement

AU - O'Reilly, Andrea

AU - Gardiner, Michael G.

AU - McMullin, Claire L.

AU - Fulton, J. Robin

AU - Coles, Martyn P.

PY - 2024/1/21

Y1 - 2024/1/21

N2 - The aluminacyclopropane K[Al(NON)(η-C 2H 4)] ([NON] 2− = [O(SiMe 2NDipp) 2] 2−, Dipp = 2,6-iPr 2C 6H 3) reacts with CO 2 and iPrN 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 C NiPr to afford ring-expanded products of C-C bond formation. The latter system undergoes a 1,3-silyl retro-Brook rearrangement of the NON-group, to afford the [NNO] 2− ligand ([NNO] 2− = [N(Dipp)SiMe 2N(Dipp)SiMe 2O] 2−). The mechanism of transformation was examined by density functional theory (DFT).

AB - The aluminacyclopropane K[Al(NON)(η-C 2H 4)] ([NON] 2− = [O(SiMe 2NDipp) 2] 2−, Dipp = 2,6-iPr 2C 6H 3) reacts with CO 2 and iPrN 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 C NiPr to afford ring-expanded products of C-C bond formation. The latter system undergoes a 1,3-silyl retro-Brook rearrangement of the NON-group, to afford the [NNO] 2− ligand ([NNO] 2− = [N(Dipp)SiMe 2N(Dipp)SiMe 2O] 2−). The mechanism of transformation was examined by density functional theory (DFT).

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U2 - 10.1039/D3CC05785B

DO - 10.1039/D3CC05785B

M3 - Article

SN - 1364-548X

VL - 60

SP - 881

EP - 884

JO - Chemical Communications

JF - Chemical Communications

IS - 7

ER -

Aluminyl derived ethene functionalization with heteroallenes, leading to an intramolecular ligand rearrangement

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