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Intramolecular addition of alkyllithiums to acetylenes: Regiospecific 4-, 5-, and 6-exo-dig cyclizations

✍ Scribed by William F. Bailey; Timo V. Ovaska

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 243 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)94585-4

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✦ Synopsis

Primary acetylenic alkylliihiums bearing a phenyl substiiueni on the triple bond, which may be prepared in virtually quantitative yield by low-temperature lithium-iodine interchange, undergo regiospecifii 8x0-dig cyclizatiin via stereoselective syn-addition of CHILi to the carbon-carbon triple bond to give four-, five-, and six-membered carbocycles bearing an easily functionalbed exocyclic lithiomethylidene moiety. Cyclization of the analogous alkyl substituted acetylenic alkyllithiums is confined to the 5-8x&&~ mode.

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