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

Kodali, Satish Babu; Jakku, Narendar Reddy; Kamatala, Chinna Rajanna; Yerraguntla, Rajeshwar Rao; Elisha, Ivon Chakravarthi

doi:10.22631/ajgc.2017.101557.1031

Document Type : Original Research Article

Authors

¹ Department of Chemistry, Rayalaseema University, Kurnool-518 007 (A.P.) India

² Department of Chemistry, Osmania University, Hyderabad (T.S)-500007 India

³ Department of Chemistry, Govt. City College, Hyderabad-500002 (T.S.) India

https://doi.org/10.22631/ajgc.2017.101557.1031

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).

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Asian Journal of Green Chemistry

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

References

References

Volume 2, Issue 1 - Serial Number 1
January 2018
Pages 70-84

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

References

References

Volume 2, Issue 1 - Serial Number 1January 2018Pages 70-84

Volume 2, Issue 1 - Serial Number 1
January 2018
Pages 70-84