Stereocontrolled oxidation of a thiacalix[4]arene to the sulfinyl counterpart of a defined S=O configuration

Naoya Morohashi; Nobuhiko Iki; Chizuko Kabuto; Sotaro Miyano

doi:10.1016/S0040-4039(00)00313-0

Stereocontrolled oxidation of a thiacalix[4]arene to the sulfinyl counterpart of a defined S=O configuration

Naoya Morohashi, Nobuhiko Iki, Chizuko Kabuto, Sotaro Miyano

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

36 Citations (Scopus)

Abstract

Treatment of p-tert-butylthiacalix[4]arene (1) with benzyl bromide in THF-DMF using Nail as the base catalyst afforded the tetrabenzyl ether of cone conformation (4(C)) as the major product, oxidation of which, with NaBO₃ in CHCl₃-acetic acid, proceeded readily to give the corresponding sulfinyl compound (5) with the four S=O groups disposed on the same side of the plane defined by the macrocyclic ring probably to avoid the steric hindrance imposed by the benzyllic moieties. Cleavage of the ether bonds gave a new stereoisomer of p-tertbutylsulfinylcalix[4]arene (2(ccc)) with the four S=O groups arranged in a cis-cis-cis configuration. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	2933-2937
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	16
DOIs	https://doi.org/10.1016/S0040-4039(00)00313-0
Publication status	Published - 2000 Apr 15
Externally published	Yes

Keywords

Calixarenes
Oxidation
Sulfinyl compounds
X-ray crystallography

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)00313-0

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title = "Stereocontrolled oxidation of a thiacalix[4]arene to the sulfinyl counterpart of a defined S=O configuration",

abstract = "Treatment of p-tert-butylthiacalix[4]arene (1) with benzyl bromide in THF-DMF using Nail as the base catalyst afforded the tetrabenzyl ether of cone conformation (4(C)) as the major product, oxidation of which, with NaBO3 in CHCl3-acetic acid, proceeded readily to give the corresponding sulfinyl compound (5) with the four S=O groups disposed on the same side of the plane defined by the macrocyclic ring probably to avoid the steric hindrance imposed by the benzyllic moieties. Cleavage of the ether bonds gave a new stereoisomer of p-tertbutylsulfinylcalix[4]arene (2(ccc)) with the four S=O groups arranged in a cis-cis-cis configuration. (C) 2000 Elsevier Science Ltd.",

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

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

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

year = "2000",

month = apr,

day = "15",

doi = "10.1016/S0040-4039(00)00313-0",

language = "English",

volume = "41",

pages = "2933--2937",

journal = "Tetrahedron Letters",

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T1 - Stereocontrolled oxidation of a thiacalix[4]arene to the sulfinyl counterpart of a defined S=O configuration

AU - Morohashi, Naoya

AU - Iki, Nobuhiko

AU - Kabuto, Chizuko

AU - Miyano, Sotaro

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

PY - 2000/4/15

Y1 - 2000/4/15

N2 - Treatment of p-tert-butylthiacalix[4]arene (1) with benzyl bromide in THF-DMF using Nail as the base catalyst afforded the tetrabenzyl ether of cone conformation (4(C)) as the major product, oxidation of which, with NaBO3 in CHCl3-acetic acid, proceeded readily to give the corresponding sulfinyl compound (5) with the four S=O groups disposed on the same side of the plane defined by the macrocyclic ring probably to avoid the steric hindrance imposed by the benzyllic moieties. Cleavage of the ether bonds gave a new stereoisomer of p-tertbutylsulfinylcalix[4]arene (2(ccc)) with the four S=O groups arranged in a cis-cis-cis configuration. (C) 2000 Elsevier Science Ltd.

AB - Treatment of p-tert-butylthiacalix[4]arene (1) with benzyl bromide in THF-DMF using Nail as the base catalyst afforded the tetrabenzyl ether of cone conformation (4(C)) as the major product, oxidation of which, with NaBO3 in CHCl3-acetic acid, proceeded readily to give the corresponding sulfinyl compound (5) with the four S=O groups disposed on the same side of the plane defined by the macrocyclic ring probably to avoid the steric hindrance imposed by the benzyllic moieties. Cleavage of the ether bonds gave a new stereoisomer of p-tertbutylsulfinylcalix[4]arene (2(ccc)) with the four S=O groups arranged in a cis-cis-cis configuration. (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)00313-0

DO - 10.1016/S0040-4039(00)00313-0

M3 - Article

AN - SCOPUS:0034655490

VL - 41

SP - 2933

EP - 2937

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 16

ER -

Stereocontrolled oxidation of a thiacalix[4]arene to the sulfinyl counterpart of a defined S=O configuration

Abstract

Keywords

ASJC Scopus subject areas

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