A decisive electronic effect of a bridgehead methoxy substituent on the electrophilic cage opening of 1,3-bishomocubanones |
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| Authors: | AJH Klunder GJA Ariaans B Zwanenburg |
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| Institution: | Department of Organic Chemistry, University of Nijmegen, Toernooiveld, 6525 Ed Nijmegen, The Netherlands |
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| Abstract: | 4-Methoxypentacyclo5.3.0.02,5.03,9.0,4,8] decan-6-ones 4 and 9 undergo an acid catalysed cage fragmentation to give tricyclodecenediones 6 and 10, respectively. With silver cations under basic conditions, an unusual oxidative cage fission reaction is observed leading to tetracyclo4.3.0.02,403,8]nonan-5-one 7-carboxylic acids. |
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