Novel molecular chirality in the calixarene family: Formation of chiral disulfinyldithiacalix[4]arenes via partial oxidation of two adjacent sulfides of tetrathiacalix[4]arene

Naoya Morohashi; Nobuhiko Iki; Toru Onodera; Chizuko Kabuto; Sotaro Miyano

doi:10.1016/S0040-4039(00)00780-2

Novel molecular chirality in the calixarene family: Formation of chiral disulfinyldithiacalix[4]arenes via partial oxidation of two adjacent sulfides of tetrathiacalix[4]arene

Naoya Morohashi, Nobuhiko Iki, Toru Onodera, Chizuko Kabuto, Sotaro Miyano

Tohoku University

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

34 Citations (Scopus)

Abstract

The first chiral disulfinyldithiacalix[4]arenes have been obtained by oxidation of two adjacent epithio groups of the tetramethyl ether of tetra(p- tert-butyl)tetrathiacalix[4]arene. The chiral resolution was achieved by HPLC using Chiralpak AD as a stationary phase. Furthermore, the absolute configuration of these compounds was determined by X-ray crystallography. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	5093-5097
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4039(00)00780-2
Publication status	Published - 2000 Jun 24

Keywords

Calixarenes
Oxidation
Sulfinyl compounds
X-ray crystallography

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10.1016/S0040-4039(00)00780-2

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title = "Novel molecular chirality in the calixarene family: Formation of chiral disulfinyldithiacalix[4]arenes via partial oxidation of two adjacent sulfides of tetrathiacalix[4]arene",

abstract = "The first chiral disulfinyldithiacalix[4]arenes have been obtained by oxidation of two adjacent epithio groups of the tetramethyl ether of tetra(p- tert-butyl)tetrathiacalix[4]arene. The chiral resolution was achieved by HPLC using Chiralpak AD as a stationary phase. Furthermore, the absolute configuration of these compounds was determined by X-ray crystallography. (C) 2000 Elsevier Science Ltd.",

keywords = "Calixarenes, Oxidation, Sulfinyl compounds, X-ray crystallography",

author = "Naoya Morohashi and Nobuhiko Iki and Toru Onodera and Chizuko Kabuto and Sotaro Miyano",

note = "Funding Information: This work was partially supported by a Grant-in-Aid for Scientific Research on Priority Areas (No. 10208202) from the Ministry of Education, Science, Sports and Culture, Japan.",

year = "2000",

month = jun,

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doi = "10.1016/S0040-4039(00)00780-2",

language = "English",

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pages = "5093--5097",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Novel molecular chirality in the calixarene family

T2 - Formation of chiral disulfinyldithiacalix[4]arenes via partial oxidation of two adjacent sulfides of tetrathiacalix[4]arene

AU - Morohashi, Naoya

AU - Iki, Nobuhiko

AU - Onodera, Toru

AU - Kabuto, Chizuko

AU - Miyano, Sotaro

N1 - Funding Information: This work was partially supported by a Grant-in-Aid for Scientific Research on Priority Areas (No. 10208202) from the Ministry of Education, Science, Sports and Culture, Japan.

PY - 2000/6/24

Y1 - 2000/6/24

N2 - The first chiral disulfinyldithiacalix[4]arenes have been obtained by oxidation of two adjacent epithio groups of the tetramethyl ether of tetra(p- tert-butyl)tetrathiacalix[4]arene. The chiral resolution was achieved by HPLC using Chiralpak AD as a stationary phase. Furthermore, the absolute configuration of these compounds was determined by X-ray crystallography. (C) 2000 Elsevier Science Ltd.

AB - The first chiral disulfinyldithiacalix[4]arenes have been obtained by oxidation of two adjacent epithio groups of the tetramethyl ether of tetra(p- tert-butyl)tetrathiacalix[4]arene. The chiral resolution was achieved by HPLC using Chiralpak AD as a stationary phase. Furthermore, the absolute configuration of these compounds was determined by X-ray crystallography. (C) 2000 Elsevier Science Ltd.

KW - Calixarenes

KW - Oxidation

KW - Sulfinyl compounds

KW - X-ray crystallography

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U2 - 10.1016/S0040-4039(00)00780-2

DO - 10.1016/S0040-4039(00)00780-2

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SN - 0040-4039

VL - 41

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EP - 5097

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Novel molecular chirality in the calixarene family: Formation of chiral disulfinyldithiacalix[4]arenes via partial oxidation of two adjacent sulfides of tetrathiacalix[4]arene

Abstract

Keywords

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