Abstract
A simple method for selective acylation of protected and unprotected hydroxylamines
with bis- and tetrakis-substituted p-tert- butylcalix[4]arene-acids through amide bond formation via mixed anhydrides is presented.
The first crystal structure of calix-hydroxamate 1 is presented.
Key words
calix[4]arene-hydroxamates - calix[4]arene-amides - synthesis - mixed anhydride method
References
<A NAME="RP03206SS-1A">1a </A>
Nagasaki T.
Shinkai S.
Matsuda TJ.
J. Chem. Soc., Perkin Trans. 1
1990,
2617
<A NAME="RP03206SS-1B">1b </A>
Nagasaki T.
Shinkai S.
J. Chem. Soc., Perkin Trans. 2
1991,
1063
<A NAME="RP03206SS-2">2 </A>
Dasaradhi L.
Stark PC.
Huber VJ.
Smith PH.
Jarvinen GD.
Gopalan AS.
J. Chem. Soc., Perkin Trans. 2
1997,
1187
<A NAME="RP03206SS-3">3 </A>
Hutchinson S.
Kearney GA.
Horne E.
Lynch B.
Glennon JD.
McKervey MA.
Harris SJ.
Anal. Chim. Acta
1994,
291:
269
<A NAME="RP03206SS-4">4 </A>
Harris SJ,
MacManus MG, and
Guthrie J. inventors; Eur. Patent 309291.
; Chem. Abstr. 1989, 111, 117298e
<A NAME="RP03206SS-5">5 </A>
Hamdi A.
Abidi R.
Asfari Z.
Vicents J.
J. Incl. Phenom.
2003,
45:
99
<A NAME="RP03206SS-6">6 </A>
Canevet Ch.
Libman J.
Shanzer A.
Angew. Chem., Int. Ed. Engl.
1996,
22:
2657
<A NAME="RP03206SS-7">7 </A>
Nagasaki T.
Shinkai S.
Bull. Chem. Soc. Jpn.
1992,
65:
471
<A NAME="RP03206SS-8">8 </A>
Glennon JD.
Hutchinson S.
Harris SJ.
Walker A.
McKervey MA.
McSweeney CC.
Anal. Chem.
1997,
69:
2207
<A NAME="RP03206SS-9">9 </A>
Pochini A.
Ungaro R.
Andreetti GD.
Calestani G.
Ugozzoli F.
J. Incl. Phenom.
1984,
2:
199
<A NAME="RP03206SS-10">10 </A>
Arnaud-Neu F.
Barrett G.
Cremin S.
Deasy M.
Ferguson G.
Harris SJ.
Lough AJ.
Guerra L.
McKervey MA.
Schwing-Weill MJ.
Schwinte P.
J. Chem. Soc., Perkin Trans. 2
1992,
1119
<A NAME="RP03206SS-11">11 </A>
Reddy AS.
Kumar MS.
Reddy GR.
Tetrahedron Lett.
2000,
41:
6285
<A NAME="RP03206SS-12">12 </A>
Smukste I.
Smithrud DB.
Tetrahedron
2001,
57:
9555
<A NAME="RP03206SS-13">13 </A>
Bocheńska M.
Banach R.
Zielińska A.
Kravtsov VCh.
J. Incl. Phenom.
2001,
39:
219
<A NAME="RP03206SS-14">14 </A>
Arduini A.
Ghidini E.
Pochini A.
Ungaro R.
Andreetti GD.
Calestani G.
Ugozzoli F.
J. Incl. Phenom.
1988,
6:
119
<A NAME="RP03206SS-15">15 </A>
Bocheńska M, and
Lesińska U. inventors; Polish Pat. Appl. P0375856. Synthesis of calix[4]arene-hydroxamates
and new compounds:
<A NAME="RP03206SS-16">16 </A>
Iwamoto K.
Shinkai S.
J. Org. Chem.
1992,
57:
7066
<A NAME="RP03206SS-17">17 </A>
Casnati A.
Pochini A.
Ungaro R.
Ugozzoli F.
Arnaud F.
Fanni S.
Schwing MJ.
Egberink RJM.
de Jong F.
Reinhoudt DN.
J. Am. Chem. Soc.
1995,
117:
2767
<A NAME="RP03206SS-18">18 </A>
Bocheńska M.
Zielińska A.
Pomecko R.
Hubscher-Bruder V.
Arnaud-Neu F.
J. Incl. Phenom.
2005,
52:
129
<A NAME="RP03206SS-19">19 </A>
Scheldrick GM.
SHELX-97: Program for the solution and refinement of the crystal structures
University of Göttingen;
Germany:
1997.
<A NAME="RP03206SS-20">20 </A>
Crystallographic data for the structure of 1 reported in this paper have been deposited with Cambridge Crystallographic Data Centre
as supplementary publication No. CCDC-275710 (fwd). Copies of the data can be obtained
free of charge on application to CCDC, 12, Union Road, Cambridge, UK (E-mail: deposit@ccdc.cam.ac.uk).