期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 71, 期 26, 页码 9877-9879出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo061680c
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We have previously reported an efficient synthesis of beta-phenylselenium-substituted butenolides via electrophilic cyclization of 2,3-allenoates with PhSeCl in aqueous MeCN. However, when 2,3-allenoates were treated with PhSeCl in MeCN, 3-phenylseleno-4-oxo-2(E)-alkenoates were formed unexpectedly. The addition of Li2CO3 improved the yield and the selectivity of the reaction. A possible mechanism involving a decomposition of selenate esters was proposed.
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