The Journal of Organic Chemistry

Nucleophilic aromatic substitution with elimination in a dinitrosalicylic lactone or ester via Meisenheimer intermediates

PR Jones, SD Rothenberger

Index: Jones, Paul R.; Rothenberger, Scott D. Journal of Organic Chemistry, 1986 , vol. 51, # 15 p. 3016 - 3023

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Citation Number: 6

Abstract

The “spiro” Meisenheimer complex B, as its K salt, came from either lb or 2b and 1 equiv of K thiophenolate or KCN in MeOH. In no case were we able to isolate the bicyclo Meisenheimer complex C, which would have formed by nucleophile attack on lb without subsequent ring opening.