標題: Ozonolysis of bis-endo-diacylbicyclo[2.2.1]heptenes in dichloromethane-methanol
作者: Lin, Hui-Chang
Lin, Chu-Chung
Wu, Hsien-Jen
應用化學系
Department of Applied Chemistry
關鍵字: Ozonolysis;Bis-endo-diacylbicyclo[2.2.1]heptenes
公開日期: 23-Sep-2011
摘要: Ozonolysis of bis-endo-diacylbicyclo[2.2.1]heptenes 3a-d at -78 degrees C in dichloromethane methanol gave the hydroperoxides 6a-d in 70-80% yields. Ozonolysis of bis-endo-diacetylbicyclo[2.2.2]octene 15 and bis-endo-diacetyl-7-oxabicyclo-[2.2.1]heptene 16 under the same reaction conditions gave the hydroperoxides 17 and 18, respectively. The intramolecular sequential nucleophilic addition of the carbonyl groups to the carbonyl oxide group was observed for the first time and was found to be faster than the intermolecular nucleophilic addition of a methanol molecule to the carbonyl oxide group. Ozonolysis of compound 23 in CH(2)Cl(2)-MeOH at -78 degrees C followed by reduction with Me(2)S gave compounds 24 and 25, in which the stereochemistry of the methoxyl groups was determined by X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.
URI: http://dx.doi.org/10.1016/j.tet.2011.07.055
http://hdl.handle.net/11536/19082
ISSN: 0040-4020
DOI: 10.1016/j.tet.2011.07.055
期刊: TETRAHEDRON
Volume: 67
Issue: 38
起始頁: 7236
結束頁: 7243
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