Journal
TETRAHEDRON LETTERS
Volume 48, Issue 30, Pages 5265-5268Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.05.133
Keywords
thiophenol; AlBN; [3,3] sigmatropic rearrangement; radical cyclization; dihydrofurocoumarin; dihydropyranocoumarin
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Regioselective synthesis of dihydrofurocoumarins and dihydropyranocoumarins in excellent yields from 4-prop-2-ynyloxy coumarin via a thiol mediated radical reaction is described. Alkenyl radicals are generated from easily available terminal alkynes and thiophenol. Thiophenol catalyzed the Claisen rearrangement of the 4-prop-2-ynyloxycoumarin ethers. (c) 2007 Elsevier Ltd. All rights reserved.
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