A 1,3-sigmatropic rearrangement revealed in the solid and solution state structures of a chiral sodium 1-azaallyl complex derived from (S)-N-(α-methylbenzyl)allylamine

Philip C Andrews; Simone M Calleja; Melissa Maguire; Peter J Nichols

doi:10.1002/1099-0682(200207)2002:7<1583::AID-EJIC1583>3.0.CO;2-J

A 1,3-sigmatropic rearrangement revealed in the solid and solution state structures of a chiral sodium 1-azaallyl complex derived from (S)-N-(α-methylbenzyl)allylamine

Philip C Andrews, Simone M Calleja, Melissa Maguire, Peter J Nichols

School of Chemistry

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

15 Citations (Scopus)

Abstract

The reaction of nBuNa with (S)-N-(α-methylbenzyl)allylamine, followed by the addition of tmeda, gives a chiral sodium 1-azaallyl complex, {[(S)-α-[PhC(H)MeN..-C-(H)..-CHCH₃)] Na·tmeda}₂, as confirmed by single crystal X-ray diffraction and solution NMR spectroscopy, and is most likely the result of a 1,3-sigmatropic rearrangement and subsequent delocalisation within the resulting enamide.

Original language	English
Pages (from-to)	1583-1587
Number of pages	5
Journal	European Journal of Inorganic Chemistry
Volume	7
DOIs	https://doi.org/10.1002/1099-0682(200207)2002:7<1583::AID-EJIC1583>3.0.CO;2-J
Publication status	Published - 1 Jan 2002

Keywords

Amines
Chirality
N ligands
Sigmatropic rearrangement
Sodium
Structure elucidation

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10.1002/1099-0682(200207)2002:7<1583::AID-EJIC1583>3.0.CO;2-J

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Andrews, P. C., Calleja, S. M., Maguire, M., & Nichols, P. J. (2002). A 1,3-sigmatropic rearrangement revealed in the solid and solution state structures of a chiral sodium 1-azaallyl complex derived from (S)-N-(α-methylbenzyl)allylamine. European Journal of Inorganic Chemistry, 7, 1583-1587. https://doi.org/10.1002/1099-0682(200207)2002:7<1583::AID-EJIC1583>3.0.CO;2-J

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title = "A 1,3-sigmatropic rearrangement revealed in the solid and solution state structures of a chiral sodium 1-azaallyl complex derived from (S)-N-(α-methylbenzyl)allylamine",

abstract = "The reaction of nBuNa with (S)-N-(α-methylbenzyl)allylamine, followed by the addition of tmeda, gives a chiral sodium 1-azaallyl complex, {[(S)-α-[PhC(H)MeN..-C-(H)..-CHCH3)] Na·tmeda}2, as confirmed by single crystal X-ray diffraction and solution NMR spectroscopy, and is most likely the result of a 1,3-sigmatropic rearrangement and subsequent delocalisation within the resulting enamide.",

keywords = "Amines, Chirality, N ligands, Sigmatropic rearrangement, Sodium, Structure elucidation",

author = "Andrews, {Philip C} and Calleja, {Simone M} and Melissa Maguire and Nichols, {Peter J}",

year = "2002",

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doi = "10.1002/1099-0682(200207)2002:7<1583::AID-EJIC1583>3.0.CO;2-J",

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Andrews, PC, Calleja, SM, Maguire, M & Nichols, PJ 2002, 'A 1,3-sigmatropic rearrangement revealed in the solid and solution state structures of a chiral sodium 1-azaallyl complex derived from (S)-N-(α-methylbenzyl)allylamine', European Journal of Inorganic Chemistry, vol. 7, pp. 1583-1587. https://doi.org/10.1002/1099-0682(200207)2002:7<1583::AID-EJIC1583>3.0.CO;2-J

A 1,3-sigmatropic rearrangement revealed in the solid and solution state structures of a chiral sodium 1-azaallyl complex derived from (S)-N-(α-methylbenzyl)allylamine. / Andrews, Philip C; Calleja, Simone M; Maguire, Melissa; Nichols, Peter J.

In: European Journal of Inorganic Chemistry, Vol. 7, 01.01.2002, p. 1583-1587.

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

TY - JOUR

T1 - A 1,3-sigmatropic rearrangement revealed in the solid and solution state structures of a chiral sodium 1-azaallyl complex derived from (S)-N-(α-methylbenzyl)allylamine

AU - Andrews, Philip C

AU - Calleja, Simone M

AU - Maguire, Melissa

AU - Nichols, Peter J

PY - 2002/1/1

Y1 - 2002/1/1

N2 - The reaction of nBuNa with (S)-N-(α-methylbenzyl)allylamine, followed by the addition of tmeda, gives a chiral sodium 1-azaallyl complex, {[(S)-α-[PhC(H)MeN..-C-(H)..-CHCH3)] Na·tmeda}2, as confirmed by single crystal X-ray diffraction and solution NMR spectroscopy, and is most likely the result of a 1,3-sigmatropic rearrangement and subsequent delocalisation within the resulting enamide.

AB - The reaction of nBuNa with (S)-N-(α-methylbenzyl)allylamine, followed by the addition of tmeda, gives a chiral sodium 1-azaallyl complex, {[(S)-α-[PhC(H)MeN..-C-(H)..-CHCH3)] Na·tmeda}2, as confirmed by single crystal X-ray diffraction and solution NMR spectroscopy, and is most likely the result of a 1,3-sigmatropic rearrangement and subsequent delocalisation within the resulting enamide.

KW - Amines

KW - Chirality

KW - N ligands

KW - Sigmatropic rearrangement

KW - Sodium

KW - Structure elucidation

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U2 - 10.1002/1099-0682(200207)2002:7<1583::AID-EJIC1583>3.0.CO;2-J

DO - 10.1002/1099-0682(200207)2002:7<1583::AID-EJIC1583>3.0.CO;2-J

M3 - Article

VL - 7

SP - 1583

EP - 1587

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

SN - 1434-1948

ER -

A 1,3-sigmatropic rearrangement revealed in the solid and solution state structures of a chiral sodium 1-azaallyl complex derived from (S)-N-(α-methylbenzyl)allylamine

Abstract

Keywords

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