Demas, M., Javadi, G.J., Bradley, L.M. and Hunt, D.A. (2000) Metalation of a 3,5-Dichloro-Tertiary Benzamide. An Unusual Regioselectivity Observation. The Journal of Organic Chemistry, 65, 7201-7202.
http://dx.doi.org/10.1021/jo000160t

has been cited by the following article:

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

  AUTHORS: Francesca Khani, Tina Fleming, Carleton Collins, Erica Tabakin, Lynn M. Bradley, David A. Hunt

  KEYWORDS: Directed Ortho-Metalation, Complex-Induced Proximity Effects (CIPE), 3, 5-Dichlorobenzamides

  JOURNAL NAME: International Journal of Organic Chemistry, Vol.6 No.2, June 3, 2016

  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.