Addition of isopropyllithium in diethyl ether to. alpha.-substituted styrenes. Quantitative evidence on the stability of cyclopropylcarbinyllithium species

JA Landgrebe, JD Shoemaker

Index: Landgrebe,J.A.; Shoemaker,J.D. Journal of the American Chemical Society, 1967 , vol. 89, # 17 p. 4465 - 4472

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Citation Number: 12

Abstract

Abstract: The relative rates of addition of isopropyllithium in diethyl ether at-45" to a series of a-substituted styrenes in which the substituent was ethyl (la), isopropyl (lb), 3-pentyl (k), cyclopropyl (Id), and trans-2-cis-3-dimethylcyclopropyl (le) were? 8.0, 1.0, 0.6, 310, and 115, respectively. The product of addition of isopropyllithium to Id after hydrolysis was 4-phenyl- Zmethyl-cis-4-heptene (6) while addition to le followed by hydrolysis produced a mixture ...