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Synthesis and Application of Iso(thio)cyanate-Functionalized Calix[4]arenes (1997)

van Wageningen, André M. A. ; Snip, Erwin ; Verboom, Willem ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 2235-2245

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ISSN: 0947-3440

Keywords: Calix[4]arenes ; Cavitands ; Iso(thio)cyanates ; Carbamates ; (Thio)ureas ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719971110

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