Convenient direct synthesis of bisformylated calix[4]arenes via ipso substitution

被引：42

作者：

Chawla, H. M. ^{[1
]}

Pant, N. ^{[1
]}

Srivastava, Bindu ^{[1
]}

Upreti, Shailesh ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, New Delhi 110016, India

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 11期

关键词：

D O I：

10.1021/ol0605124

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthesis of bisformylated calix[4]arenes via ipso substitution of p-tert-butylcalix[4] arenes through treatment with hexamethylenetetramine/ trifluoroacetic acid is described. Under identical conditions, p-tert-butylcalix[4] arene tetramethyl ether 4 gives proximally substituted bisformylated derivative 4a in a pinched cone conformation.

引用

页码：2237 / 2240

页数：4

共 21 条

[1] DIRECT REGIOSELECTIVE FORMYLATION OF TETRAALKOXYCALIX[4]ARENES FIXED IN THE CONE CONFORMATION AND SYNTHESIS OF NEW CAVITANDS [J].

ARDUINI, A ;

FANNI, S ;

MANFREDI, G ;

POCHINI, A ;

UNGARO, R ;

SICURI, AR ;

UGOZZOLI, F .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1448-1453

[2] Synthesis of selectively formylated calixarene ethers [J].

Arora, V ;

Chawla, HM ;

Santra, A .

TETRAHEDRON, 2002, 58 (28) :5591-5597

[3] Boradiazaindacene-appended calix[4]arene: Fluorescence sensing of pH near neutrality [J].

Baki, CN ;

Akkaya, EU .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1512-1513

[4] Regioselective ipso formylation of p-tert-butylcafix[4]arene [J].

Chawla, HM ;

Pant, N ;

Srivastava, B .

TETRAHEDRON LETTERS, 2005, 46 (42) :7259-7262

[5]

Collins E.M., 1991, J CHEM SOC P1, V12, P3137

[6] Glycoside-clustering round calixarenes toward the development of multivalent carbohydrate ligands. synthesis and conformational analysis of calix[4]arene O- and C-glycoconjugates [J].

Alessandro, D ;

Kleban, M ;

Hu, XB ;

Marra, A ;

Banks, HD .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4722-4733

[7]

Gutsche C.D., 1989, MONOGRAPHS SUPRAMOLE

[8]

Gutsche C. D, 1998, MONOGRAPHS SUPRAMOLE

[9] CALIXARENES-9 - CONFORMATIONAL ISOMERS OF THE ETHERS AND ESTERS OF CALIX[4]ARENES [J].

GUTSCHE, CD ;

DHAWAN, B ;

LEVINE, JA ;

NO, KH ;

BAUER, LJ .

TETRAHEDRON, 1983, 39 (03) :409-426

[10] Synthesis and binding studies of multiple calix[4]arenes [J].

Hwang, GT ;

Kim, BH .

TETRAHEDRON, 2002, 58 (44) :9019-9028

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