Isolation and structural characterisation of [{(Me3Si)2NMg[µ-OC(H)Ph2] ·(OCPh2)}2], an intermediate in the -hydride transfer reaction between an alkyl(amido)magnesium and benzophenone

K.W. Henderson, J.F. Allan, A.R. Kennedy

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Abstract

The in situ reaction of Bu2Mg with 2 mol. equiv. of (Me3Si)2NH followed by addition of Ph2CO yields the heteroleptic amide/alkoxide complex [{(Me3Si)2NMg[µ-OC(H)Ph2] ·(OCPh2)}2] 1, whereas reaction of purified [{(Me3Si)2N}2Mg] 2 with Ph2CO results in formation of the solvate [{(Me3Si)2N}2Mg·(O CPh2)2] 3, the difference being due to incomplete amination of the bis(alkyl)magnesium compound resulting in -hydride transfer to the ketone, which is the first example of this type of transformation using an alkyl(amido)magnesium reagent.
Original languageEnglish
Pages (from-to)1149-1150
Number of pages1
JournalJournal of the Chemical Society, Chemical Communications
Volume1997
Issue number12
DOIs
Publication statusPublished - 1997

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Magnesium Compounds
Amination
Ketones
Amides
Magnesium
benzophenone

Keywords

  • heteroleptic amide/alkoxide complex
  • solvate
  • ketone
  • magnesium reagent

Cite this

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title = "Isolation and structural characterisation of [{(Me3Si)2NMg[µ-OC(H)Ph2] ·(OCPh2)}2], an intermediate in the -hydride transfer reaction between an alkyl(amido)magnesium and benzophenone",
abstract = "The in situ reaction of Bu2Mg with 2 mol. equiv. of (Me3Si)2NH followed by addition of Ph2CO yields the heteroleptic amide/alkoxide complex [{(Me3Si)2NMg[µ-OC(H)Ph2] ·(OCPh2)}2] 1, whereas reaction of purified [{(Me3Si)2N}2Mg] 2 with Ph2CO results in formation of the solvate [{(Me3Si)2N}2Mg·(O CPh2)2] 3, the difference being due to incomplete amination of the bis(alkyl)magnesium compound resulting in -hydride transfer to the ketone, which is the first example of this type of transformation using an alkyl(amido)magnesium reagent.",
keywords = "heteroleptic amide/alkoxide complex, solvate, ketone, magnesium reagent",
author = "K.W. Henderson and J.F. Allan and A.R. Kennedy",
year = "1997",
doi = "10.1039/a701875d",
language = "English",
volume = "1997",
pages = "1149--1150",
journal = "Journal of the Chemical Society, Chemical Communications",
issn = "0022-4936",
number = "12",

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TY - JOUR

T1 - Isolation and structural characterisation of [{(Me3Si)2NMg[µ-OC(H)Ph2] ·(OCPh2)}2], an intermediate in the -hydride transfer reaction between an alkyl(amido)magnesium and benzophenone

AU - Henderson, K.W.

AU - Allan, J.F.

AU - Kennedy, A.R.

PY - 1997

Y1 - 1997

N2 - The in situ reaction of Bu2Mg with 2 mol. equiv. of (Me3Si)2NH followed by addition of Ph2CO yields the heteroleptic amide/alkoxide complex [{(Me3Si)2NMg[µ-OC(H)Ph2] ·(OCPh2)}2] 1, whereas reaction of purified [{(Me3Si)2N}2Mg] 2 with Ph2CO results in formation of the solvate [{(Me3Si)2N}2Mg·(O CPh2)2] 3, the difference being due to incomplete amination of the bis(alkyl)magnesium compound resulting in -hydride transfer to the ketone, which is the first example of this type of transformation using an alkyl(amido)magnesium reagent.

AB - The in situ reaction of Bu2Mg with 2 mol. equiv. of (Me3Si)2NH followed by addition of Ph2CO yields the heteroleptic amide/alkoxide complex [{(Me3Si)2NMg[µ-OC(H)Ph2] ·(OCPh2)}2] 1, whereas reaction of purified [{(Me3Si)2N}2Mg] 2 with Ph2CO results in formation of the solvate [{(Me3Si)2N}2Mg·(O CPh2)2] 3, the difference being due to incomplete amination of the bis(alkyl)magnesium compound resulting in -hydride transfer to the ketone, which is the first example of this type of transformation using an alkyl(amido)magnesium reagent.

KW - heteroleptic amide/alkoxide complex

KW - solvate

KW - ketone

KW - magnesium reagent

UR - http://dx.doi.org/10.1039/a701875d

U2 - 10.1039/a701875d

DO - 10.1039/a701875d

M3 - Article

VL - 1997

SP - 1149

EP - 1150

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

SN - 0022-4936

IS - 12

ER -