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
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
收藏
页码:3899 / 3902
页数:4
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