142075-30-7

Upstream product

• 98-88-4 benzoyl chloride 
• 31562-40-0 tert-butyl tert-butanethiosulfinate 
• 1696-17-9 N,N-diethylbenzamide 
• 62076-10-2 (tert-butylsulfinyl)benzene 
• 88-10-8 N,N-diethylcarbamyl chloride 

Relevant academic research and scientific papers

Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation

Directed metallation and sulfinylation yields sulfoxides which undergo ipso nucleophilic aromatic substitution with tertiary and secondary alkyllithiums, giving aromatic rings bearing alkyl groups generally incompatible with directed metallation methods and with regioselectivity complementary with classical Friedel-Crafts substitution. The Royal Society of Chemistry 2006.

The tert-butyl sulfoxide directed ortho metalation group. New synthetic methodology for substituted aromatics and pyridines and comparison with other metalation directors

Details of the directed ortho metalation of tert-butyl phenyl sulfoxide (1) and 2- and 4-tert-butyl pyridyl sulfoxides (3a,b) are described along with comparisons with established metalation directors (CONR2, OCONR2, OMOM, SO2t-Bu) via inter- and intramolecular competition experiments.