Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 30, Pages 9164-9174Publisher
WILEY-BLACKWELL
DOI: 10.1002/chem.201001105
Keywords
alkynes; carbenoids; cyclization; iodine; lithium
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Alkylative carbocyclization reactions of omega-iodoalkynyl tosylates with alkynyllithium compounds to give products with incorporated iodine atoms are described. Slow addition of 2-(3-iodoprop-2-ynyloxy)ethyl tosylates to 1-alkynyllithium compounds in letrahydrofuran at 40 degrees C followed by additional stirring at this temperature gives (Z)-3-(1-iodoprop-2-ynylidene)tetrahydrofurans stereoselectively in good to moderate yields. Under similar conditions at 0 degrees C, 4-iodobut-1-ynyl tosylates react with 1-alkynyllithium compounds to give (1-iodoprop-2-ynylidene)cyclopropanes. The carbocyclization reactions are proposed to proceed through a new carbenoid-chain process involving the exo cyclization of a lithium acetylide intermediate and the vinylic substitution of the resulting TsO,Li-cyclo-alkylidenecarbenoids (Ts = tosyl) by 1-alkynyllithium compounds.
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