The formylation of the upper-rims of thiacalixarenes: synthesis of the first tetra-formylated and the first meta-substituted thiacalix[4]arenes

Vadim Kessler; C Desroches; S Parola

doi:10.1016/j.tetlet.2004.06.078

The formylation of the upper-rims of thiacalixarenes: synthesis of the first tetra-formylated and the first meta-substituted thiacalix[4]arenes

Vadim Kessler
, C Desroches
, S Parola

Publication: Contribution to journal › Journal article › peer-review

Abstract

The conventional Gross reaction for the formylation of the tetrapropoxythiacalix[4]arene using TiCl4 affords the 18-(chloromethyl)-28-hydroxy-25,26,27-tripropoxythiacalix[4]arene substituted in the meta-position of the macrocycle. The p-tetraformyl-tetrapropoxythiacalix[4]arene, which is an interesting intermediate to the upper-rims functionalization of thiacalixarenes, was prepared with a very good yield using BuLi and N-formylpiperidine. (C) 2004 Published by Elsevier Ltd.

Original language	English
Pages (from-to)	6329-6331
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2004.06.078
Publication status	Published - 2004

Keywords

calixarene
formylation
chloromethylation
meta-substitution

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10.1016/j.tetlet.2004.06.078

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title = "The formylation of the upper-rims of thiacalixarenes: synthesis of the first tetra-formylated and the first meta-substituted thiacalix[4]arenes",

abstract = "The conventional Gross reaction for the formylation of the tetrapropoxythiacalix[4]arene using TiCl4 affords the 18-(chloromethyl)-28-hydroxy-25,26,27-tripropoxythiacalix[4]arene substituted in the meta-position of the macrocycle. The p-tetraformyl-tetrapropoxythiacalix[4]arene, which is an interesting intermediate to the upper-rims functionalization of thiacalixarenes, was prepared with a very good yield using BuLi and N-formylpiperidine. (C) 2004 Published by Elsevier Ltd.",

keywords = "calixarene, formylation, chloromethylation, meta-substitution, calixarene, formylation, chloromethylation, meta-substitution",

author = "Vadim Kessler and C Desroches and S Parola",

year = "2004",

doi = "10.1016/j.tetlet.2004.06.078",

language = "English",

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pages = "6329--6331",

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T1 - The formylation of the upper-rims of thiacalixarenes: synthesis of the first tetra-formylated and the first meta-substituted thiacalix[4]arenes

AU - Kessler, Vadim

AU - Desroches, C

AU - Parola, S

PY - 2004

Y1 - 2004

N2 - The conventional Gross reaction for the formylation of the tetrapropoxythiacalix[4]arene using TiCl4 affords the 18-(chloromethyl)-28-hydroxy-25,26,27-tripropoxythiacalix[4]arene substituted in the meta-position of the macrocycle. The p-tetraformyl-tetrapropoxythiacalix[4]arene, which is an interesting intermediate to the upper-rims functionalization of thiacalixarenes, was prepared with a very good yield using BuLi and N-formylpiperidine. (C) 2004 Published by Elsevier Ltd.

AB - The conventional Gross reaction for the formylation of the tetrapropoxythiacalix[4]arene using TiCl4 affords the 18-(chloromethyl)-28-hydroxy-25,26,27-tripropoxythiacalix[4]arene substituted in the meta-position of the macrocycle. The p-tetraformyl-tetrapropoxythiacalix[4]arene, which is an interesting intermediate to the upper-rims functionalization of thiacalixarenes, was prepared with a very good yield using BuLi and N-formylpiperidine. (C) 2004 Published by Elsevier Ltd.

KW - calixarene

KW - formylation

KW - chloromethylation

KW - meta-substitution

KW - calixarene

KW - formylation

KW - chloromethylation

KW - meta-substitution

UR - https://res.slu.se/id/publ/2915

U2 - 10.1016/j.tetlet.2004.06.078

DO - 10.1016/j.tetlet.2004.06.078

M3 - Journal article

SN - 0040-4039

VL - 45

SP - 6329

EP - 6331

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

The formylation of the upper-rims of thiacalixarenes: synthesis of the first tetra-formylated and the first meta-substituted thiacalix[4]arenes

Abstract

Keywords

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