A combination of NMR, kinetic, and computational methods are used to examine reactions of lithium diethylamide in tetrahydrofuran (THF) with n-dodecyl bromide and n-octyl benzenesulfonate. The alkyl bromide undergoes competitive S(N)2 substitution and E2 elimination in proportions independent of all concentrations except for a minor medium effect. Rate studies show that both reactions occur via...

Efficient C-H functionalization requires selectivity for specific C-H bonds. Progress has been made for directed aromatic substitution reactions to achieve ortho and meta selectivity, but a general strategy for para-selective C-H functionalization has remained elusive. Herein we introduce a previously unappreciated concept that enables nearly complete para selectivity. We propose that radicals ...

Sulfate attack is a series of physico-chemical reactions between hardened cement paste and sulfate ions. Sulfate ion penetration into the hydrated cement results in the formation of voluminous and deleterious phases such as gypsum and ettringite which are believed to cause deterioration and expansion of concrete. Concrete deterioration due to sulfate attack depends on many parameters, however, ...

A general, efficient, and sustainable method for nucleophilic aromatic substitution reactions in water using a cellulose-based additive was developed.