Rotational isomerism in 2,4,6-tri-tert-butylanilides

Nobutaka Ototake; Isao Takahashi; Shiori Tsukagoshi; Tatsuki Maeda; Osamu Kitagawa

doi:10.1016/j.tet.2012.11.096

Rotational isomerism in 2,4,6-tri-tert-butylanilides

Nobutaka Ototake, Isao Takahashi, Shiori Tsukagoshi, Tatsuki Maeda, Osamu Kitagawa

研究成果: Article › 査読

1 被引用数 (Scopus)

抄録

Z-Rotamers of several 2,4,6-tri-tert-butylanilides slowly isomerize at rt in CDCl₃ to E-rotamers, yielding equilibrium mixtures of Z- and E-rotamers after standing for 1 week. The equilibrium ratios between the anilide rotamers in the solution depend strongly on the bulkiness of the acyl substituents as well as the formation of intramolecular hydrogen bond. Heating equilibrium mixtures in the solid state produced complete isomerization to the Z-rotamer.

本文言語	English
ページ（範囲）	1013-1016
ページ数	4
ジャーナル	Tetrahedron
巻	69
号	3
DOI	https://doi.org/10.1016/j.tet.2012.11.096
出版ステータス	Published - 2013 1月 21

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/j.tet.2012.11.096

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title = "Rotational isomerism in 2,4,6-tri-tert-butylanilides",

abstract = "Z-Rotamers of several 2,4,6-tri-tert-butylanilides slowly isomerize at rt in CDCl3 to E-rotamers, yielding equilibrium mixtures of Z- and E-rotamers after standing for 1 week. The equilibrium ratios between the anilide rotamers in the solution depend strongly on the bulkiness of the acyl substituents as well as the formation of intramolecular hydrogen bond. Heating equilibrium mixtures in the solid state produced complete isomerization to the Z-rotamer.",

keywords = "Amides, Anilides, Hydrogen bonding, Isomerization, Rotamers",

author = "Nobutaka Ototake and Isao Takahashi and Shiori Tsukagoshi and Tatsuki Maeda and Osamu Kitagawa",

year = "2013",

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day = "21",

doi = "10.1016/j.tet.2012.11.096",

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T1 - Rotational isomerism in 2,4,6-tri-tert-butylanilides

AU - Ototake, Nobutaka

AU - Takahashi, Isao

AU - Tsukagoshi, Shiori

AU - Maeda, Tatsuki

AU - Kitagawa, Osamu

PY - 2013/1/21

Y1 - 2013/1/21

N2 - Z-Rotamers of several 2,4,6-tri-tert-butylanilides slowly isomerize at rt in CDCl3 to E-rotamers, yielding equilibrium mixtures of Z- and E-rotamers after standing for 1 week. The equilibrium ratios between the anilide rotamers in the solution depend strongly on the bulkiness of the acyl substituents as well as the formation of intramolecular hydrogen bond. Heating equilibrium mixtures in the solid state produced complete isomerization to the Z-rotamer.

AB - Z-Rotamers of several 2,4,6-tri-tert-butylanilides slowly isomerize at rt in CDCl3 to E-rotamers, yielding equilibrium mixtures of Z- and E-rotamers after standing for 1 week. The equilibrium ratios between the anilide rotamers in the solution depend strongly on the bulkiness of the acyl substituents as well as the formation of intramolecular hydrogen bond. Heating equilibrium mixtures in the solid state produced complete isomerization to the Z-rotamer.

KW - Amides

KW - Anilides

KW - Hydrogen bonding

KW - Isomerization

KW - Rotamers

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DO - 10.1016/j.tet.2012.11.096

M3 - Article

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VL - 69

SP - 1013

EP - 1016

JO - Tetrahedron

JF - Tetrahedron

IS - 3

ER -

Rotational isomerism in 2,4,6-tri-tert-butylanilides

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