A general method for obtaining calix[4]arene derivatives in the 1,2-alternate conformation

Petr Slavík; Václav Eigner; Pavel Lhoták

doi:10.1016/j.tet.2016.08.028

A general method for obtaining calix[4]arene derivatives in the 1,2-alternate conformation

Petr Slavík, Václav Eigner, Pavel Lhoták^*

^*Corresponding author for this work

Chemistry

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

Abstract

The 1,2-alternate conformation, so far the least accessible atropisomer of calix[4]arene, is now easily available on a gram scale. The entire synthetic sequence consists of only two steps—(a) proximal dialkylation (R¹-I, NaH/DMF), and (b) another subsequent dialkylation (R²-I, Me₃SiOK/THF). The selection of appropriate base/solvent combinations in both stages was the key prerequisite for the successful preparation of the 1,2-alternate conformers, which are available without the use of any protecting groups.

Original language	English
Pages (from-to)	6348-6355
Number of pages	8
Journal	Tetrahedron
Volume	72
Issue number	41
Early online date	13 Aug 2016
DOIs	https://doi.org/10.1016/j.tet.2016.08.028
Publication status	Published - 13 Oct 2016

Keywords

1,2-Alternate
Alkylation
Calixarene
Conformation
Conformational mobility
Partial cone

Access to Document

10.1016/j.tet.2016.08.028

Cite this

@article{efb480b7c2ec4c9da6a628b8b0a3ac60,

title = "A general method for obtaining calix[4]arene derivatives in the 1,2-alternate conformation",

abstract = "The 1,2-alternate conformation, so far the least accessible atropisomer of calix[4]arene, is now easily available on a gram scale. The entire synthetic sequence consists of only two steps—(a) proximal dialkylation (R1-I, NaH/DMF), and (b) another subsequent dialkylation (R2-I, Me3SiOK/THF). The selection of appropriate base/solvent combinations in both stages was the key prerequisite for the successful preparation of the 1,2-alternate conformers, which are available without the use of any protecting groups.",

keywords = "1,2-Alternate, Alkylation, Calixarene, Conformation, Conformational mobility, Partial cone",

author = "Petr Slav{\'i}k and V{\'a}clav Eigner and Pavel Lhot{\'a}k",

year = "2016",

month = oct,

day = "13",

doi = "10.1016/j.tet.2016.08.028",

language = "English",

volume = "72",

pages = "6348--6355",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "41",

}

TY - JOUR

T1 - A general method for obtaining calix[4]arene derivatives in the 1,2-alternate conformation

AU - Slavík, Petr

AU - Eigner, Václav

AU - Lhoták, Pavel

PY - 2016/10/13

Y1 - 2016/10/13

N2 - The 1,2-alternate conformation, so far the least accessible atropisomer of calix[4]arene, is now easily available on a gram scale. The entire synthetic sequence consists of only two steps—(a) proximal dialkylation (R1-I, NaH/DMF), and (b) another subsequent dialkylation (R2-I, Me3SiOK/THF). The selection of appropriate base/solvent combinations in both stages was the key prerequisite for the successful preparation of the 1,2-alternate conformers, which are available without the use of any protecting groups.

AB - The 1,2-alternate conformation, so far the least accessible atropisomer of calix[4]arene, is now easily available on a gram scale. The entire synthetic sequence consists of only two steps—(a) proximal dialkylation (R1-I, NaH/DMF), and (b) another subsequent dialkylation (R2-I, Me3SiOK/THF). The selection of appropriate base/solvent combinations in both stages was the key prerequisite for the successful preparation of the 1,2-alternate conformers, which are available without the use of any protecting groups.

KW - 1,2-Alternate

KW - Alkylation

KW - Calixarene

KW - Conformation

KW - Conformational mobility

KW - Partial cone

UR - http://www.scopus.com/inward/record.url?scp=84987974360&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2016.08.028

DO - 10.1016/j.tet.2016.08.028

M3 - Article

AN - SCOPUS:84987974360

SN - 0040-4020

VL - 72

SP - 6348

EP - 6355

JO - Tetrahedron

JF - Tetrahedron

IS - 41

ER -

A general method for obtaining calix[4]arene derivatives in the 1,2-alternate conformation

Abstract

Keywords

Access to Document

Other files and links

Cite this