Deprotonation/alkylation reactions of monoalkyl-9, 10-dihydroanthracenes and-7, 12-dihydropleiadenes. Stereochemical outcome and anion models

…, Z Marcinow, PW Rabideau

Index: Mooney, Jennifer L.; Marcinow, Zbigniew; Rabideau, Peter W. Journal of Organic Chemistry, 1986 , vol. 51, # 4 p. 527 - 532

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Citation Number: 4

Abstract

The alkylation stereochemistry of 9-alkyl-10-lithio-9, lO-dihydroanthracene has often been explained on the basis of inverting, boabshaped anion models. Recent carbon-13 NMR data for these anions has led to the suggestion of a flattened, sp2-hybridized model, and alkylation studies herein are presented in support of this model. Since recent molecular mechanics calculations have indicated a wide range of central ring folding for 9, lO- ...