SYNTHESIS OF MONOALKYLATED CALIX[4]ARENES VIA DIRECT ALKYLATION

被引：109

作者：

GROENEN, LC

RUEL, BHM

CASNATI, A

VERBOOM, W

POCHINI, A

UNGARO, R

REINHOUDT, DN

机构：

[1] UNIV TWENTE,ORGAN CHEM LAB,POB 217,7500 AE ENSCHEDE,NETHERLANDS

[2] UNIV PARMA,INST ORGAN CHEM,I-43100 PARMA,ITALY

来源：

TETRAHEDRON | 1991年 / 47卷 / 39期

关键词：

CALIX[4]ARENES; O-ALKYLATION; BASE EFFECT; ANION REACTIVITY;

D O I：

10.1016/S0040-4020(01)96179-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new one-step procedure for the synthesis of monoalkylated calix[4]arenes is presented. Reaction of calix[4]arene 1a or 1b with 1.2 equivalent of a weak base (K2CO3 in MeCN or CsF in DMF) and excess of alkylating agent affords the monoalkylated calix[4]arenes in moderate to good yields.

引用

收藏

页码：8379 / 8384

页数：6

相关论文

共 17 条

[1] PKA OF CALIXARENES AND ANALOGS IN NONAQUEOUS SOLVENTS [J].

ARAKI, K ;

IWAMOTO, K ;

SHINKAI, S ;

MATSUDA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (12) :3480-3485

[2]

BOHMER V, 1984, MAKROMOL CHEM-RAPID, V5, P221

[3] CALIX[4]ARENES WITH PYRIDINE PENDANT GROUPS - REGIOSELECTIVE PROXIMAL ALKYLATION AT THE LOWER RIM [J].

BOTTINO, F ;

GIUNTA, L ;

PAPPALARDO, S .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23) :5407-5409

[4] A GENERAL-SYNTHESIS OF CALIX[4]ARENE MONOALKYL ETHERS [J].

CASNATI, A ;

ARDUINI, A ;

GHIDINI, E ;

POCHINI, A ;

UNGARO, R .

TETRAHEDRON, 1991, 47 (12-13) :2221-2228

[5] FLUORIDE-ION AS A BASE IN ORGANIC-SYNTHESIS [J].

CLARK, JH .

CHEMICAL REVIEWS, 1980, 80 (05) :429-452

[6] MOLECULAR RECEPTORS WITH THE CALIX[4]ARENE SUBSTRUCTURE - SYNTHESIS OF DERIVATIVES WITH MIXED LIGATING FUNCTIONAL-GROUPS [J].

COLLINS, EM ;

MCKERVEY, MA ;

HARRIS, SJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (02) :372-374

[7] THE 1,2-ALTERNATE CONFORMATION OF CALIX[4]ARENES - A RARE CONFORMATION - DYNAMIC H-1-NMR STUDIES OF FLEXIBLE TETRAALKYLATED CALIX[4]ARENES [J].

GROENEN, LC ;

VANLOON, JD ;

VERBOOM, W ;

HARKEMA, S ;

CASNATI, A ;

UNGARO, R ;

POCHINI, A ;

UGOZZOLI, F ;

REINHOUDT, DN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2385-2392

[8] SYN-1,2-DIALKYLATED CALIX[4]ARENES - GENERAL INTERMEDIATES IN THE NAH/DMF TETRAALKYLATION OF CALIX[4]ARENES [J].

GROENEN, LC ;

RUEL, BHM ;

CASNATI, A ;

TIMMERMAN, P ;

VERBOOM, W ;

HARKEMA, S ;

POCHINI, A ;

UNGARO, R ;

REINHOUDT, DN .

TETRAHEDRON LETTERS, 1991, 32 (23) :2675-2678

[9]

GUSCHE CD, 1989, MONOGRAPHS SUPRAMOLE, V1

[10] CALIXARENES .18. SYNTHESIS PROCEDURES FOR PARA-TERT-BUTYLCALIX[4]ARENE [J].

GUTSCHE, CD ;

IQBAL, M ;

STEWART, D .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) :742-745