Building an extended inverse crown motif via alkali-metal-mediated alpha-magnesiation of furan

D.V. Graham, E. Hevia, A.R. Kennedy, R.E. Mulvey, C.T. O'Hara, C. Talmard

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The utility of inverse crown chemistry is extended to aromatic heterocycles, as furan is deprotonated selectively at the a-position by the mixed-metal alkyl-amido base [(TMEDA)Na-.(Bu-n)(TMP)Mg(TMP)] to generate a transient intermediate which undergoes disproportionation to the disodium dimagnesium hexafuryl tri(thf) complex [{{(thf)(3)Na-.(2)}{(TMEDA)Mg-.(2)}(2-C4H3O)(6)}(infinity)], a new type of inverse crown structure with triply-stabilized (through Mg-C sigma, Na-O sigma and (NaC)-C-...-C pi interactions) furyl 'guest' anions, and the tris(amide) [(TMEDA)(x)(NaMg)-Na-.(TMP)(3)].
LanguageEnglish
Pages417-419
Number of pages2
JournalChemical Communications (London)
Volume2006
Issue number4
DOIs
Publication statusPublished - 28 Jan 2006

Fingerprint

Alkali Metals
Thymidine Monophosphate
Metals
Amides
Anions
furan

Keywords

  • deprotonation
  • base
  • chemistry
  • block
  • alkyl

Cite this

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title = "Building an extended inverse crown motif via alkali-metal-mediated alpha-magnesiation of furan",
abstract = "The utility of inverse crown chemistry is extended to aromatic heterocycles, as furan is deprotonated selectively at the a-position by the mixed-metal alkyl-amido base [(TMEDA)Na-.(Bu-n)(TMP)Mg(TMP)] to generate a transient intermediate which undergoes disproportionation to the disodium dimagnesium hexafuryl tri(thf) complex [{{(thf)(3)Na-.(2)}{(TMEDA)Mg-.(2)}(2-C4H3O)(6)}(infinity)], a new type of inverse crown structure with triply-stabilized (through Mg-C sigma, Na-O sigma and (NaC)-C-...-C pi interactions) furyl 'guest' anions, and the tris(amide) [(TMEDA)(x)(NaMg)-Na-.(TMP)(3)].",
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Building an extended inverse crown motif via alkali-metal-mediated alpha-magnesiation of furan. / Graham, D.V.; Hevia, E.; Kennedy, A.R.; Mulvey, R.E.; O'Hara, C.T.; Talmard, C.

In: Chemical Communications (London), Vol. 2006, No. 4, 28.01.2006, p. 417-419.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Building an extended inverse crown motif via alkali-metal-mediated alpha-magnesiation of furan

AU - Graham, D.V.

AU - Hevia, E.

AU - Kennedy, A.R.

AU - Mulvey, R.E.

AU - O'Hara, C.T.

AU - Talmard, C.

PY - 2006/1/28

Y1 - 2006/1/28

N2 - The utility of inverse crown chemistry is extended to aromatic heterocycles, as furan is deprotonated selectively at the a-position by the mixed-metal alkyl-amido base [(TMEDA)Na-.(Bu-n)(TMP)Mg(TMP)] to generate a transient intermediate which undergoes disproportionation to the disodium dimagnesium hexafuryl tri(thf) complex [{{(thf)(3)Na-.(2)}{(TMEDA)Mg-.(2)}(2-C4H3O)(6)}(infinity)], a new type of inverse crown structure with triply-stabilized (through Mg-C sigma, Na-O sigma and (NaC)-C-...-C pi interactions) furyl 'guest' anions, and the tris(amide) [(TMEDA)(x)(NaMg)-Na-.(TMP)(3)].

AB - The utility of inverse crown chemistry is extended to aromatic heterocycles, as furan is deprotonated selectively at the a-position by the mixed-metal alkyl-amido base [(TMEDA)Na-.(Bu-n)(TMP)Mg(TMP)] to generate a transient intermediate which undergoes disproportionation to the disodium dimagnesium hexafuryl tri(thf) complex [{{(thf)(3)Na-.(2)}{(TMEDA)Mg-.(2)}(2-C4H3O)(6)}(infinity)], a new type of inverse crown structure with triply-stabilized (through Mg-C sigma, Na-O sigma and (NaC)-C-...-C pi interactions) furyl 'guest' anions, and the tris(amide) [(TMEDA)(x)(NaMg)-Na-.(TMP)(3)].

KW - deprotonation

KW - base

KW - chemistry

KW - block

KW - alkyl

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UR - http://dx.doi.org/10.1039/b514985a

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DO - 10.1039/b514985a

M3 - Article

VL - 2006

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EP - 419

JO - Chemical Communications (London)

T2 - Chemical Communications (London)

JF - Chemical Communications (London)

SN - 0009-241X

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