標題: Synthesis of new type diacetal trioxa-cage compounds via an intramolecular nucleophilic addition of the hydroxy group to the carbonyl oxide group
作者: Wu, HJ
Chao, CS
Lin, CC
應用化學系
Department of Applied Chemistry
公開日期: 30-Oct-1998
摘要: The synthesis of diacetal trioxa-cage compounds with a new type of skeleton is reported. Ozonolysis of the diols 2a-f, 21, 24, and 33 in CH2Cl2 at -78 degrees C followed by reduction with Me2S gave the diacetal trioxa-cages 3a-f, 22, 25, and 34 in 70-80% yields, respectively. A mechanism via an intramolecular nucleophilic addition of the hydroxy group of the diols to the carbonyl oxide group is proposed for the formation of the diacetal trioxa-cages. The effect of the number of carbon atoms at the bridge of the diols on the formation of the diacetal trioxa-cage skeleton was examined. Ozonolysis of the diols 13 and 15 under the same reaction conditions gave compounds 16 and 18, respectively. No detectable amount of the trioxa-cages 17 and 19 was obtained. For the synthesis of the diacetal trioxa-cages 28a-c and 31, which possess an alkene bond intact, ozonolysis of the diols 27a-c and 30 was performed by controlling the amount of ozone.
URI: http://hdl.handle.net/11536/31810
ISSN: 0022-3263
期刊: JOURNAL OF ORGANIC CHEMISTRY
Volume: 63
Issue: 22
起始頁: 7687
結束頁: 7693
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