Proton Mobility in 2??Substituted 1, 3??Dichlorobenzenes:“ortho” or “meta” Metalation?

M Schlosser, C Heiss, E Marzi…

Index: Schlosser, Manfred; Heiss, Christophe; Marzi, Elena; Scopelliti, Rosario European Journal of Organic Chemistry, 2006 , # 19 p. 4398 - 4404

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Citation Number: 9

Abstract

Abstract Nine 1, 3-dichlorobenzene congeners were selected as model compounds to assess the relative rates of proton abstraction from 4-and 5-positions (“ortho” vs.“meta” metalation). Using lithium 2, 2, 6, 6-tetramethylpiperidide as the basic reagent, the chlorine- adjacent 4-position underwent metalation exclusively. In contrast, attack at the chlorine- remote 5-position became significant even in the case of moderately sized 2-substituents ( ...

~88%

~65%

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~91%

Detail

~99%

~48%

~13%

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~6%

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~67%

~89%

~87%

Detail

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Quantitative structure??activity analysis of larvicidal 1??(...

[Oikawa; Nakagawa; Nishimura; Ueno; Fujita Pesticide Science, 1994 , vol. 41, # 2 p. 139 - 148]