Regioselective synthesis of calix[8]crowns by direct alkylation of p-tert-butylcalix[8]arene

被引：24

作者：

Geraci, C ^{[1
]}

Piattelli, M ^{[1
]}

Neri, P ^{[1
]}

机构：

[1] CNR,IST STUDIO SOSTANZE NAT INTERESSE ALIMENTARE & CH,I-95028 VALVERDE,CT,ITALY

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 22期

关键词：

D O I：

10.1016/0040-4039(96)00684-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct alkylation of p-tert-butylcalix[8]arene with oligoethylene glycol ditosylates affords calix[8]crowns-n with a bridging pattern dependent on the nature of the base used. Alkali metal hydrides (NaH or KH) afford mainly 1,4-calix[8]crowns 2(n) in yield up to 46%, while K2CO3 and Cs2CO3 with triethylene glycol ditosylate give the 1,3-crown 4(4) and its 1,5-isomer 5(4) as the main product, respectively. Appreciable amounts of 1,2-calix[8]crowns 3(4) are formed with all bases but NaH. At room temperature the H-1 NMR spectra of compounds 2(n)-5(4) show broad signals indicative of hampered conformational mobility. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：3899 / 3902

页数：4

共 18 条

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