Regioselectivity Differentiation in Metalations of 3,5-Dichloro-Tertiary versus Secondary Benzamides

Khani, Francesca and Fleming, Tina and Collins, Carleton and Tabakin, Erica and Bradley, Lynn M. and Hunt, David A. (2016) Regioselectivity Differentiation in Metalations of 3,5-Dichloro-Tertiary versus Secondary Benzamides. International Journal of Organic Chemistry, 06 (02). pp. 142-146. ISSN 2161-4687

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Official URL: https://doi.org/10.4236/ijoc.2016.62015

Abstract

Metalation regioslectivity of 3,5-dichlorobenzamides is a function of the type of amide (secondary versus tertiary) used in the sequence. Metalation at the 2-position (adjacent to the carboxamide functional group) occurs when the secondary benzamide is metalated with sec-butyllithium/ TMEDA mediated through complex-induced proximity effects (CIPE) process, whereas metalation with sec-butyllithium/TMEDA occurs exclusively at the 4-position when the tertiary benzamide is used under identical reaction conditions.

Item Type:	Article
Subjects:	Eurolib Press > Chemical Science
Depositing User:	Managing Editor
Date Deposited:	14 Mar 2023 08:23
Last Modified:	01 Jul 2024 06:16
URI:	http://info.submit4journal.com/id/eprint/978

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