標題: Face selectivity in the photocycloaddition reactions of acrylonitrile to 5-substituted adamantan-2-ones and pyrolysis of the products to methyleneadamantanes
作者: Chung, WS
Ho, CC
交大名義發表
應用化學系
National Chiao Tung University
Department of Applied Chemistry
公開日期: 1-三月-1997
摘要: The photocycloaddition of acrylonitrile to 5-substituted adamantan-2-ones :(l-X) produces two geometrically isomeric oxetanes in which the oxygen atom and the 5-substituent are in the anti or syn positions, The substituent was varied from fluoro, chloro, bromo, hydroxy to phenyl and the product ratios were similar (ca, 60:40) in all instances, Small portions (<5%) of the oxetanes were pyrolysed when analysed by GC at above 200 degrees C, and the products from the pyrolysis were confirmed to be the corresponding methyleneadamantanes by independent syntheses, Assignment of the configuration of the oxetanes was found to be consistent with C-13 additivity scheme and the chemical shifts are more closely predicted using known oxetanes of l-X with methacrylonitrile. The product formation bias resulting from the attack on the syn-face can be explained using-the Cieplak transition state theory.
URI: http://dx.doi.org/10.1039/a606039k
http://hdl.handle.net/11536/716
ISSN: 0300-9580
DOI: 10.1039/a606039k
期刊: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Volume: 
Issue: 3
起始頁: 553
結束頁: 557
顯示於類別:期刊論文


文件中的檔案:

  1. A1997WN48100025.pdf