Quinolinium bound chromium(VI) reagents for efficient electrophilic aromatic nitration and thiocyanation reactions using sodium nitrate and ammonium thiocyanate

Abstract

Quinolinium dichromate (QDC) and quinolinium chlorochromate (QCC) were studied as efficient reagents for electrophilic aromatic nitration using sodium nitrite and thiocyanation by using ammonium thiocyanate under conventional, ultrasonic and solvent-free microwave assisted conditions. The microwave-assisted protocols exhibited remarkable rate acceleration and offered selective thiocyanation of the aromatic and heteroaromatic compounds with good yields. Addition of anionic (SDS) micelle to the reaction medium afforded considerable rate enhancements, while cationic (CTAB) and nonionic (Tx-100) micelles did not affect the rate noticeably. These protocols have were extended to regioselective thiocyanation of various aromatic compounds. Results were are completely similar to the nitration protocols. However, the reactions revealed comparatively shorter reaction times, and better yields in nitration reactions than in thiocyanation protocols. Catalytic effect of the SDS was attributed to the electrostatic stabilization of the cationic electrophile (NO2 + in nitration, and SCN + in thiocyanation). KEYWORDS