One-pot synthesis of cage-functionalized, ketal-containing crown ethers

Authors
Watson, WH Bodige, SG Marchand, AP Chong, HS
Citation
Wh. Watson et al., One-pot synthesis of cage-functionalized, ketal-containing crown ethers, STRUCT CHEM, 11(4), 2000, pp. 257-260
Citations number
14
Categorie Soggetti
Chemistry
Journal title
STRUCTURAL CHEMISTRY
ISSN journal
10400400 → ACNP
Volume
11
Issue
4
Year of publication
2000
Pages
257 - 260
Database
ISI
SICI code
1040-0400(200008)11:4<257:OSOCKC>2.0.ZU;2-X
Abstract
Acid-catalyzed reaction of pentacyclo[5.4.0.0(2,6).0(3,10).0(5.9)]undecane- 8,11-dione (1) with penta(ethylene glycol) produced two cage-functionalized , ketal-containing crown ethers, i.e., 2 and 3, in low yield. The structure of 2 was established unequivocally by direct methods. Alkali metal picrate extraction data obtained for 2 and for a structurally related model compou nd, i.e., 18-crown-6,indicate that 2 is an inefficient alkali metal picrate extracting agent.