The rate retarding effect of alkyl groups on arene metalation quantified

E Baston, Q Wang, M Schlosser

Index: Baston, Eckhard; Wang, Qian; Schlosser, Manfred Tetrahedron Letters, 2000 , vol. 41, # 5 p. 667 - 670

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Citation Number: 12

Abstract

Metalation/trapping sequences applied to relatively inert, tert-alkyl substituted arenes tend to give poor yields unless the reagent is used in high concentrations. Under optimized conditions, even 1, 4-bis (tert-butyl) benzene, 1, 1, 3, 3-tetramethylindane and 1, 1, 2, 2, 3, 3- hexamethylindane can be smoothly converted into derivatives. Competition experiments enable the quantitative assessment of tert-alkyl substituent effects on the metalation rates ...