期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 21, 页码 10636-10640出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo5019427
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资金
- Academy of Finland (AF) through its Computational Science Research Programme (LASTU)
- AF-DAAD (Deutscher Akademischer Austauschdienst) Mobility Project [1257329]
- Magnus Ehrnrooth Foundation
- University of Helsinki
Ring deuteration via the SEAr mechanism, which is usually problem-free, is found to be troublesome with methylenedioxy substituent aromatics. We report a case where the deuteration not only partially fails at one of the ortho positions but also is completely prevented by a conformation dependent effect at the other o-position. Such selectivity discrepancies are important due to the widespread occurrence of methylenedioxy substituted natural products. Density functional theory calculations were used to elucidate the exchange reaction mechanism in 1,2-dialkoxybenzenes.
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