Clean and convenient procedure for converting primary alkyl iodides and. alpha.,. omega.-diiodoalkanes into the corresponding alkyllithium derivatives by treatment …

E Negishi, DR Swanson…

Index: Negishi, Ei-ichi; Swanson, Douglas R.; Rousset, Christophe J. Journal of Organic Chemistry, 1990 , vol. 55, # 19 p. 5406 - 5409

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Citation Number: 191

Abstract

It was earlier reported that treatment of a, w-diiodoalkanes with 2.0-2.2 molar equiv of t-BuLi resulted in nearly quantitative yields of 3-through 5-numbered cyc10alkanes. l~ In the present study, treatment of a, w-diiodoalkanes containing 4-6 carbon chains with 4.0-4.2 molar equiv of t-BuLi provided the corresponding dilithioalkanes in 80-90% yields. One commonly used alternative for generating a, w-dilithioalkanes involves