Synthesis of calix[6]arenes partially functionalized at the upper rim

Alessandro Casnati; Laura Domiano; Andrea Pochini; Rocco Ungaro; Mar Carramolino; J. Oriol Magrans; Pedro M. Nieto; Javier Lopez-Prados; Pilar Prados; Javier de Mendoza; Rob G. Janssen; R.G. Janssen; Willem Verboom; David Reinhoudt

doi:10.1016/0040-4020(95)00826-T

Synthesis of calix[6]arenes partially functionalized at the upper rim

Alessandro Casnati, Laura Domiano, Andrea Pochini, Rocco Ungaro, Mar Carramolino, J. Oriol Magrans, Pedro M. Nieto, Javier Lopez-Prados, Pilar Prados, Javier de Mendoza, Rob G. Janssen, R.G. Janssen, Willem Verboom, David Reinhoudt

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Abstract

Several new examples of calix[6]arenes selectively functionalized at the upper rim are reported. Starting from calix[6]arenes 1,3,5-tri-, 1,2,4,5-tetra- and 1,2,3,4,5-pentaalkylated at the lower rim, it is possible to isolate macrocycles 2,4,6-tri-, 3,6-di- and 6-mono functionalized at the upper rim (18¿94% yield) with nitro, formyl, bromo, chloromethyl and 2-propenyl groups. Modifications of these moieties allow the synthesis of macrocycles bearing amino, amido, hydroxymethyl, carboxy, cyano and chloromethyl functions which can be used for further transformation and preparation of new molecular receptors, based on calix[6]arenes, which have different geometries. Examples of di- and triquinones on the hexameric macrocycle are also reported.

Original language	Undefined
Pages (from-to)	12699-12720
Number of pages	22
Journal	Tetrahedron
Volume	51
Issue number	51
DOIs	https://doi.org/10.1016/0040-4020(95)00826-T
Publication status	Published - 1995

Keywords

METIS-106642
IR-12395

Access to Document

10.1016/0040-4020(95)00826-T

K12395__

Cite this

@article{5fbf881ac1a54ede8be2f3342e426748,

title = "Synthesis of calix[6]arenes partially functionalized at the upper rim",

abstract = "Several new examples of calix[6]arenes selectively functionalized at the upper rim are reported. Starting from calix[6]arenes 1,3,5-tri-, 1,2,4,5-tetra- and 1,2,3,4,5-pentaalkylated at the lower rim, it is possible to isolate macrocycles 2,4,6-tri-, 3,6-di- and 6-mono functionalized at the upper rim (18¿94% yield) with nitro, formyl, bromo, chloromethyl and 2-propenyl groups. Modifications of these moieties allow the synthesis of macrocycles bearing amino, amido, hydroxymethyl, carboxy, cyano and chloromethyl functions which can be used for further transformation and preparation of new molecular receptors, based on calix[6]arenes, which have different geometries. Examples of di- and triquinones on the hexameric macrocycle are also reported.",

keywords = "METIS-106642, IR-12395",

author = "Alessandro Casnati and Laura Domiano and Andrea Pochini and Rocco Ungaro and Mar Carramolino and Magrans, {J. Oriol} and Nieto, {Pedro M.} and Javier Lopez-Prados and Pilar Prados and {de Mendoza}, Javier and Janssen, {Rob G.} and R.G. Janssen and Willem Verboom and David Reinhoudt",

year = "1995",

doi = "10.1016/0040-4020(95)00826-T",

language = "Undefined",

volume = "51",

pages = "12699--12720",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "51",

}

TY - JOUR

T1 - Synthesis of calix[6]arenes partially functionalized at the upper rim

AU - Casnati, Alessandro

AU - Domiano, Laura

AU - Pochini, Andrea

AU - Ungaro, Rocco

AU - Carramolino, Mar

AU - Magrans, J. Oriol

AU - Nieto, Pedro M.

AU - Lopez-Prados, Javier

AU - Prados, Pilar

AU - de Mendoza, Javier

AU - Janssen, Rob G.

AU - Janssen, R.G.

AU - Verboom, Willem

AU - Reinhoudt, David

PY - 1995

Y1 - 1995

N2 - Several new examples of calix[6]arenes selectively functionalized at the upper rim are reported. Starting from calix[6]arenes 1,3,5-tri-, 1,2,4,5-tetra- and 1,2,3,4,5-pentaalkylated at the lower rim, it is possible to isolate macrocycles 2,4,6-tri-, 3,6-di- and 6-mono functionalized at the upper rim (18¿94% yield) with nitro, formyl, bromo, chloromethyl and 2-propenyl groups. Modifications of these moieties allow the synthesis of macrocycles bearing amino, amido, hydroxymethyl, carboxy, cyano and chloromethyl functions which can be used for further transformation and preparation of new molecular receptors, based on calix[6]arenes, which have different geometries. Examples of di- and triquinones on the hexameric macrocycle are also reported.

AB - Several new examples of calix[6]arenes selectively functionalized at the upper rim are reported. Starting from calix[6]arenes 1,3,5-tri-, 1,2,4,5-tetra- and 1,2,3,4,5-pentaalkylated at the lower rim, it is possible to isolate macrocycles 2,4,6-tri-, 3,6-di- and 6-mono functionalized at the upper rim (18¿94% yield) with nitro, formyl, bromo, chloromethyl and 2-propenyl groups. Modifications of these moieties allow the synthesis of macrocycles bearing amino, amido, hydroxymethyl, carboxy, cyano and chloromethyl functions which can be used for further transformation and preparation of new molecular receptors, based on calix[6]arenes, which have different geometries. Examples of di- and triquinones on the hexameric macrocycle are also reported.

KW - METIS-106642

KW - IR-12395

U2 - 10.1016/0040-4020(95)00826-T

DO - 10.1016/0040-4020(95)00826-T

M3 - Article

SN - 0040-4020

VL - 51

SP - 12699

EP - 12720

JO - Tetrahedron

JF - Tetrahedron

IS - 51

ER -