Improved Halogenation of Methyl Aromatics and Methyl Heteroaromatics: Unexpected Reactivity of Tetrahalogeno-diphenylglycolurils
Florian Moretti
SRSMC, Nancy Université & CNRS Faculté des Sciences et Techniques, B.70239, F-54506 Vandoeuvre-lès-Nancy Cedex, France
Search for more papers by this authorGuillaume Poisson
SRSMC, Nancy Université & CNRS Faculté des Sciences et Techniques, B.70239, F-54506 Vandoeuvre-lès-Nancy Cedex, France
Search for more papers by this authorCorresponding Author
Alain Marsura
SRSMC, Nancy Université & CNRS Faculté des Sciences et Techniques, B.70239, F-54506 Vandoeuvre-lès-Nancy Cedex, France
Correspondence to: Alain Marsura; e-mail: [email protected].Search for more papers by this authorFlorian Moretti
SRSMC, Nancy Université & CNRS Faculté des Sciences et Techniques, B.70239, F-54506 Vandoeuvre-lès-Nancy Cedex, France
Search for more papers by this authorGuillaume Poisson
SRSMC, Nancy Université & CNRS Faculté des Sciences et Techniques, B.70239, F-54506 Vandoeuvre-lès-Nancy Cedex, France
Search for more papers by this authorCorresponding Author
Alain Marsura
SRSMC, Nancy Université & CNRS Faculté des Sciences et Techniques, B.70239, F-54506 Vandoeuvre-lès-Nancy Cedex, France
Correspondence to: Alain Marsura; e-mail: [email protected].Search for more papers by this authorABSTRACT
1,3,4,6-Tetrachloro (TCDGU) and 1,3,4,6-tetrabromo-3α,6α-diphenylglycolurils smooth halogen oxidizers have been exploited in a new direction as reagents for free radical substitution toward some N-halosuccinimide nonreactive bis-heterocycles. An unexpected selectivity and reactivity were observed with methyl benzenes, methyl heterocycles, and methyl-bis-heterocycles of interest. A chemometric study has been performed to optimize five independent factors of the chlorination reaction with TCDGU. The predictive model was established either for the halogenation conversion and the ratio of monochlorination.
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