Synthesis and application of iso(thio)cyanate-functionalized calix[4]arenes

André M.A. van Wageningen; Erwin Snip; Willem Verboom; David N. Reinhoudt; Harold Boerrigter

doi:10.1002/jlac.199719971110

Synthesis and application of iso(thio)cyanate-functionalized calix[4]arenes

André M.A. van Wageningen, Erwin Snip, Willem Verboom, David N. Reinhoudt^*, Harold Boerrigter

^*Corresponding author for this work

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Abstract

Aminocalix[4]arenes 7-12 react with triphosgene and thiophosgene to the corresponding iso(thio)cyanate-functionalized calix[4]arenes 13-20. Carbamate- (21-25) and ureasubstituted calix[4]arenes (26,27) can be obtained via isocyanatocalix[4]arenes using a one-pot synthesis starting from the corresponding aminocalix[4]arenes in moderate to good yields. Isothiocyanate-functionalized calix[4]arenes 16, 18 react selectively with amines to the corresponding thioureas 28-31 in 59-83% yield. Reaction of isothiocyanate-functionalized calix[4]arenes 16, 19, 20 with cavitands 34, 38 gives 2:2 products 42-45 in 35-42% yield.

Original language	English
Pages (from-to)	2235-2245
Journal	Liebigs Annalen
Volume	1997
Issue number	11
DOIs	https://doi.org/10.1002/jlac.199719971110
Publication status	Published - 1997

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title = "Synthesis and application of iso(thio)cyanate-functionalized calix[4]arenes",

abstract = "Aminocalix[4]arenes 7-12 react with triphosgene and thiophosgene to the corresponding iso(thio)cyanate-functionalized calix[4]arenes 13-20. Carbamate- (21-25) and ureasubstituted calix[4]arenes (26,27) can be obtained via isocyanatocalix[4]arenes using a one-pot synthesis starting from the corresponding aminocalix[4]arenes in moderate to good yields. Isothiocyanate-functionalized calix[4]arenes 16, 18 react selectively with amines to the corresponding thioureas 28-31 in 59-83% yield. Reaction of isothiocyanate-functionalized calix[4]arenes 16, 19, 20 with cavitands 34, 38 gives 2:2 products 42-45 in 35-42% yield.",

author = "{van Wageningen}, {Andr{\'e} M.A.} and Erwin Snip and Willem Verboom and Reinhoudt, {David N.} and Harold Boerrigter",

year = "1997",

doi = "10.1002/jlac.199719971110",

language = "English",

volume = "1997",

pages = "2235--2245",

journal = "Liebigs Annalen",

issn = "0947-3440",

publisher = "Wiley-VCH Verlag",

number = "11",

}

TY - JOUR

T1 - Synthesis and application of iso(thio)cyanate-functionalized calix[4]arenes

AU - van Wageningen, André M.A.

AU - Snip, Erwin

AU - Verboom, Willem

AU - Reinhoudt, David N.

AU - Boerrigter, Harold

PY - 1997

Y1 - 1997

N2 - Aminocalix[4]arenes 7-12 react with triphosgene and thiophosgene to the corresponding iso(thio)cyanate-functionalized calix[4]arenes 13-20. Carbamate- (21-25) and ureasubstituted calix[4]arenes (26,27) can be obtained via isocyanatocalix[4]arenes using a one-pot synthesis starting from the corresponding aminocalix[4]arenes in moderate to good yields. Isothiocyanate-functionalized calix[4]arenes 16, 18 react selectively with amines to the corresponding thioureas 28-31 in 59-83% yield. Reaction of isothiocyanate-functionalized calix[4]arenes 16, 19, 20 with cavitands 34, 38 gives 2:2 products 42-45 in 35-42% yield.

AB - Aminocalix[4]arenes 7-12 react with triphosgene and thiophosgene to the corresponding iso(thio)cyanate-functionalized calix[4]arenes 13-20. Carbamate- (21-25) and ureasubstituted calix[4]arenes (26,27) can be obtained via isocyanatocalix[4]arenes using a one-pot synthesis starting from the corresponding aminocalix[4]arenes in moderate to good yields. Isothiocyanate-functionalized calix[4]arenes 16, 18 react selectively with amines to the corresponding thioureas 28-31 in 59-83% yield. Reaction of isothiocyanate-functionalized calix[4]arenes 16, 19, 20 with cavitands 34, 38 gives 2:2 products 42-45 in 35-42% yield.

U2 - 10.1002/jlac.199719971110

DO - 10.1002/jlac.199719971110

M3 - Article

SN - 0947-3440

VL - 1997

SP - 2235

EP - 2245

JO - Liebigs Annalen

JF - Liebigs Annalen

IS - 11

ER -

Synthesis and application of iso(thio)cyanate-functionalized calix[4]arenes

Abstract

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