Structures and reactions of 1,3-diamidodilithium complexes: the hemisolvated l-[{CMe2\{CHMeN(R)\}(2)Li-2} center dot {OEt2]}, the unsolvated 1 : 1 mixed organo-amidolithium u-[{CMe2\{CHMeN(R} ')\}(2)center dot Li-2 center dot({nBuLi)(2)]}, and the product of oxidative ring closure, the pyrazolidine l-[({RNCHMe)(2)CMe2]} (R=2-{iPr-C6H4;} R '=2,6-{iPr(2)-C6H3)}

D T Carey; F S Mair; R G Pritchard; J E Warren; R J Woods

doi:10.1002/ejic.200390237

Structures and reactions of 1,3-diamidodilithium complexes: the hemisolvated l-[{CMe2\{CHMeN(R)\}(2)Li-2} center dot {OEt2]}, the unsolvated 1 : 1 mixed organo-amidolithium u-[{CMe2\{CHMeN(R} ')\}(2)center dot Li-2 center dot({nBuLi)(2)]}, and the product of oxidative ring closure, the pyrazolidine l-[({RNCHMe)(2)CMe2]} (R=2-{iPr-C6H4;} R '=2,6-{iPr(2)-C6H3)}

D T Carey
, F S Mair
, R G Pritchard
, J E Warren
, R J Woods

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

Abstract

The hemi-solvated C-2-symmetric 1,3-diamidolithium 1-[{CMe2\{CHMeN(R)\}(2)(Li2OEt2)-O-.]} has been crystallographically characterized. It reacts with oxygen to form the N-N ring-closed pyrazolidine 1-[({RNCHMe)(2)CMe2].} The slightly bulkier C-s-symmetric amidolithium u-[{CMe2\{CHMeN(R')\}(2)Li-.(2)]} forms an unsolvated 1:2 heterocubane complex with {nBuLi} in the solid state and in solution, as determined by X-ray crystallography and multinuclear {NMR} spectroscopy (R = 2-{iPr-C6H4;} R' = 2,6-{iPr(2)-C6H3).} ((C) Wiley-{VCH} Verlag {GmbH} \& Co. {KGaA}, 69451 Weinheim, Germany, 2003).

Original language	English
Pages (from-to)	3464-3471
Number of pages	8
Journal	European Journal of Inorganic Chemistry
DOIs	https://doi.org/10.1002/ejic.200390237
Publication status	Published - Sept 2003

Keywords

ALKYLATION
ALPHA-OLEFINS
{ALPHA-OLEFINS
{AMIDE
ASYMMETRIC
ASYMMETRIC} {ALKYLATION} {REACTIONS
carbanions
CHELATING
CHEMISTRY
CHIRAL
CHIRAL} {LITHIUM} {AMIDE
{CHIRAL} {LITHIUM} {AMIDE
ASYMMETRIC ALKYLATION REACTIONS
{COMPLEXES
CRYSTAL-STRUCTURE
{CRYSTAL-STRUCTURE
DIAMIDE
DIAMIDE} {COMPLEXES
{DIAMIDE} {COMPLEXES
N-BUTYLLITHIUM
ligands
LI-N
{LI-N
LITHIUM
lithium
N
N ligands
NMR
{NMR
{REACTIONS
SOLID-STATE
solid-state structures
{STRUCTURES
TERT-BUTYLLITHIUM
{TERT-BUTYLLITHIUM

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Carey, D. T., Mair, F. S., Pritchard, R. G., Warren, J. E., & Woods, R. J. (2003). Structures and reactions of 1,3-diamidodilithium complexes: the hemisolvated l-[{CMe2\{CHMeN(R)\}(2)Li-2} center dot {OEt2]}, the unsolvated 1 : 1 mixed organo-amidolithium u-[{CMe2\{CHMeN(R} ')\}(2)center dot Li-2 center dot({nBuLi)(2)]}, and the product of oxidative ring closure, the pyrazolidine l-[({RNCHMe)(2)CMe2]} (R=2-{iPr-C6H4;} R '=2,6-{iPr(2)-C6H3)}. European Journal of Inorganic Chemistry, 3464-3471. https://doi.org/10.1002/ejic.200390237

Carey, D T ; Mair, F S ; Pritchard, R G et al. / Structures and reactions of 1,3-diamidodilithium complexes: the hemisolvated l-[{CMe2\{CHMeN(R)\}(2)Li-2} center dot {OEt2]}, the unsolvated 1 : 1 mixed organo-amidolithium u-[{CMe2\{CHMeN(R} ')\}(2)center dot Li-2 center dot({nBuLi)(2)]}, and the product of oxidative ring closure, the pyrazolidine l-[({RNCHMe)(2)CMe2]} (R=2-{iPr-C6H4;} R '=2,6-{iPr(2)-C6H3)}. In: European Journal of Inorganic Chemistry. 2003 ; pp. 3464-3471.

@article{cfaacd5eb54f465ba5f7c3348f402778,

title = "Structures and reactions of 1,3-diamidodilithium complexes: the hemisolvated l-[\{CMe2\textbackslash{}\{CHMeN(R)\textbackslash{}\}(2)Li-2\} center dot \{OEt2]\}, the unsolvated 1 : 1 mixed organo-amidolithium u-[\{CMe2\textbackslash{}\{CHMeN(R\} ')\textbackslash{}\}(2)center dot Li-2 center dot(\{nBuLi)(2)]\}, and the product of oxidative ring closure, the pyrazolidine l-[(\{RNCHMe)(2)CMe2]\} (R=2-\{iPr-C6H4;\} R '=2,6-\{iPr(2)-C6H3)\}",

abstract = "The hemi-solvated C-2-symmetric 1,3-diamidolithium 1-[\{CMe2\textbackslash{}\{CHMeN(R)\textbackslash{}\}(2)(Li2OEt2)-O-.]\} has been crystallographically characterized. It reacts with oxygen to form the N-N ring-closed pyrazolidine 1-[(\{RNCHMe)(2)CMe2].\} The slightly bulkier C-s-symmetric amidolithium u-[\{CMe2\textbackslash{}\{CHMeN(R')\textbackslash{}\}(2)Li-.(2)]\} forms an unsolvated 1:2 heterocubane complex with \{nBuLi\} in the solid state and in solution, as determined by X-ray crystallography and multinuclear \{NMR\} spectroscopy (R = 2-\{iPr-C6H4;\} R' = 2,6-\{iPr(2)-C6H3).\} ((C) Wiley-\{VCH\} Verlag \{GmbH\} \textbackslash{}\& Co. \{KGaA\}, 69451 Weinheim, Germany, 2003).",

keywords = "ALKYLATION, ALPHA-OLEFINS, \{ALPHA-OLEFINS, \{AMIDE, ASYMMETRIC, ASYMMETRIC\} \{ALKYLATION\} \{REACTIONS, carbanions, CHELATING, CHEMISTRY, CHIRAL, CHIRAL\} \{LITHIUM\} \{AMIDE, \{CHIRAL\} \{LITHIUM\} \{AMIDE, ASYMMETRIC ALKYLATION REACTIONS, \{COMPLEXES, CRYSTAL-STRUCTURE, \{CRYSTAL-STRUCTURE, DIAMIDE, DIAMIDE\} \{COMPLEXES, \{DIAMIDE\} \{COMPLEXES, N-BUTYLLITHIUM, ligands, LI-N, \{LI-N, LITHIUM, lithium, N, N ligands, NMR, \{NMR, \{REACTIONS, SOLID-STATE, solid-state structures, \{STRUCTURES, TERT-BUTYLLITHIUM, \{TERT-BUTYLLITHIUM",

author = "Carey, \{D T\} and Mair, \{F S\} and Pritchard, \{R G\} and Warren, \{J E\} and Woods, \{R J\}",

note = "18",

year = "2003",

month = sep,

doi = "10.1002/ejic.200390237",

language = "English",

pages = "3464--3471",

journal = "European Journal of Inorganic Chemistry",

issn = "1099-0682",

publisher = "John Wiley \& Sons Ltd",

}

Carey, DT, Mair, FS, Pritchard, RG, Warren, JE & Woods, RJ 2003, 'Structures and reactions of 1,3-diamidodilithium complexes: the hemisolvated l-[{CMe2\{CHMeN(R)\}(2)Li-2} center dot {OEt2]}, the unsolvated 1 : 1 mixed organo-amidolithium u-[{CMe2\{CHMeN(R} ')\}(2)center dot Li-2 center dot({nBuLi)(2)]}, and the product of oxidative ring closure, the pyrazolidine l-[({RNCHMe)(2)CMe2]} (R=2-{iPr-C6H4;} R '=2,6-{iPr(2)-C6H3)}', European Journal of Inorganic Chemistry, pp. 3464-3471. https://doi.org/10.1002/ejic.200390237

Structures and reactions of 1,3-diamidodilithium complexes: the hemisolvated l-[{CMe2\{CHMeN(R)\}(2)Li-2} center dot {OEt2]}, the unsolvated 1 : 1 mixed organo-amidolithium u-[{CMe2\{CHMeN(R} ')\}(2)center dot Li-2 center dot({nBuLi)(2)]}, and the product of oxidative ring closure, the pyrazolidine l-[({RNCHMe)(2)CMe2]} (R=2-{iPr-C6H4;} R '=2,6-{iPr(2)-C6H3)}. / Carey, D T; Mair, F S; Pritchard, R G et al.
In: European Journal of Inorganic Chemistry, 09.2003, p. 3464-3471.

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

TY - JOUR

T1 - Structures and reactions of 1,3-diamidodilithium complexes: the hemisolvated l-[{CMe2\{CHMeN(R)\}(2)Li-2} center dot {OEt2]}, the unsolvated 1 : 1 mixed organo-amidolithium u-[{CMe2\{CHMeN(R} ')\}(2)center dot Li-2 center dot({nBuLi)(2)]}, and the product of oxidative ring closure, the pyrazolidine l-[({RNCHMe)(2)CMe2]} (R=2-{iPr-C6H4;} R '=2,6-{iPr(2)-C6H3)}

AU - Carey, D T

AU - Mair, F S

AU - Pritchard, R G

AU - Warren, J E

AU - Woods, R J

N1 - 18

PY - 2003/9

Y1 - 2003/9

N2 - The hemi-solvated C-2-symmetric 1,3-diamidolithium 1-[{CMe2\{CHMeN(R)\}(2)(Li2OEt2)-O-.]} has been crystallographically characterized. It reacts with oxygen to form the N-N ring-closed pyrazolidine 1-[({RNCHMe)(2)CMe2].} The slightly bulkier C-s-symmetric amidolithium u-[{CMe2\{CHMeN(R')\}(2)Li-.(2)]} forms an unsolvated 1:2 heterocubane complex with {nBuLi} in the solid state and in solution, as determined by X-ray crystallography and multinuclear {NMR} spectroscopy (R = 2-{iPr-C6H4;} R' = 2,6-{iPr(2)-C6H3).} ((C) Wiley-{VCH} Verlag {GmbH} \& Co. {KGaA}, 69451 Weinheim, Germany, 2003).

AB - The hemi-solvated C-2-symmetric 1,3-diamidolithium 1-[{CMe2\{CHMeN(R)\}(2)(Li2OEt2)-O-.]} has been crystallographically characterized. It reacts with oxygen to form the N-N ring-closed pyrazolidine 1-[({RNCHMe)(2)CMe2].} The slightly bulkier C-s-symmetric amidolithium u-[{CMe2\{CHMeN(R')\}(2)Li-.(2)]} forms an unsolvated 1:2 heterocubane complex with {nBuLi} in the solid state and in solution, as determined by X-ray crystallography and multinuclear {NMR} spectroscopy (R = 2-{iPr-C6H4;} R' = 2,6-{iPr(2)-C6H3).} ((C) Wiley-{VCH} Verlag {GmbH} \& Co. {KGaA}, 69451 Weinheim, Germany, 2003).

KW - ALKYLATION

KW - ALPHA-OLEFINS

KW - {ALPHA-OLEFINS

KW - {AMIDE

KW - ASYMMETRIC

KW - ASYMMETRIC} {ALKYLATION} {REACTIONS

KW - carbanions

KW - CHELATING

KW - CHEMISTRY

KW - CHIRAL

KW - CHIRAL} {LITHIUM} {AMIDE

KW - {CHIRAL} {LITHIUM} {AMIDE

KW - ASYMMETRIC ALKYLATION REACTIONS

KW - {COMPLEXES

KW - CRYSTAL-STRUCTURE

KW - {CRYSTAL-STRUCTURE

KW - DIAMIDE

KW - DIAMIDE} {COMPLEXES

KW - {DIAMIDE} {COMPLEXES

KW - N-BUTYLLITHIUM

KW - ligands

KW - LI-N

KW - {LI-N

KW - LITHIUM

KW - lithium

KW - N

KW - N ligands

KW - NMR

KW - {NMR

KW - {REACTIONS

KW - SOLID-STATE

KW - solid-state structures

KW - {STRUCTURES

KW - TERT-BUTYLLITHIUM

KW - {TERT-BUTYLLITHIUM

U2 - 10.1002/ejic.200390237

DO - 10.1002/ejic.200390237

M3 - Article

SN - 1099-0682

SP - 3464

EP - 3471

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

ER -

Carey DT, Mair FS, Pritchard RG, Warren JE, Woods RJ. Structures and reactions of 1,3-diamidodilithium complexes: the hemisolvated l-[{CMe2\{CHMeN(R)\}(2)Li-2} center dot {OEt2]}, the unsolvated 1 : 1 mixed organo-amidolithium u-[{CMe2\{CHMeN(R} ')\}(2)center dot Li-2 center dot({nBuLi)(2)]}, and the product of oxidative ring closure, the pyrazolidine l-[({RNCHMe)(2)CMe2]} (R=2-{iPr-C6H4;} R '=2,6-{iPr(2)-C6H3)}. European Journal of Inorganic Chemistry. 2003 Sept;3464-3471. doi: 10.1002/ejic.200390237