Bifunctional conjunctive reagents: 5-chloro-2-lithio-1-pentene and related substances. A methylenecyclohexane annulation method

…, BWA Yeung, FF Fleming

Index: Piers, Edward; Yeung, Bik Wah Anissa; Fleming, Fraser F. Canadian Journal of Chemistry, 1993 , vol. 71, # 3 p. 280 - 286

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Citation Number: 24

Abstract

The development of a new, synthetically useful methylenecyclohexane annulation method is described. Transmetallation (MeLi, tetrahydrofuran,-78° C) of 5-chloro-2-trimethylstannyl-1- pentene (8) affords the novel bifunctional reagent 5-chloro-2-lithio-1-pentene (9), which, at temperatures higher than approximately-50° C, self-destructs to give methylenecyclobutane (14). Reagent 9 can be converted into the Grignard reagent 10 and the organocopper (I) ...