Synthesis and characterization of 4-fluorophenylazoisobutyronitrile

Travis W. Vatland, Winona State University

Abstract

Phenyl Radicals (Ph•) are known to rapidly abstract hydrogens and add to double bonds in their role as reactive reaction intermediates. p-Fluorophenyl radicals (FPh•) react similarly to unsubstituted phenyl radicals and can be tracked by F-19 NMR spectroscopy, facilitating mechanistic studies. However, due to their unique nature, identifying and synthesizing sources of FPh• is a challenge. In this study we synthesized and characterized the FPh• precursor 4-fluorophenylazoisobutyronitrile (FPAIN). To synthesize FPAIN, phenylhydrazine hydrochloride was suspended in 2M NaOH, extracted with diethyl ether, dried with Na2SO4, and then reacted with acetone cyanohydrin (C4HNO). The crystalline product was reacted with potassium permanganate (KMnO4) to form FPAIN, which was thoroughly characterized by two-dimensional nuclear magnetic resonance (2D NMR), infrared spectrometry (IR), high resolution mass spectrometry (HRMS), and gas chromatography mass spectrometry (GC-MS).

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Apr 20th, 2:00 PM Apr 20th, 3:00 PM

Synthesis and characterization of 4-fluorophenylazoisobutyronitrile

Kryzsko Commons Ballroom, Winona, Minnesota

Phenyl Radicals (Ph•) are known to rapidly abstract hydrogens and add to double bonds in their role as reactive reaction intermediates. p-Fluorophenyl radicals (FPh•) react similarly to unsubstituted phenyl radicals and can be tracked by F-19 NMR spectroscopy, facilitating mechanistic studies. However, due to their unique nature, identifying and synthesizing sources of FPh• is a challenge. In this study we synthesized and characterized the FPh• precursor 4-fluorophenylazoisobutyronitrile (FPAIN). To synthesize FPAIN, phenylhydrazine hydrochloride was suspended in 2M NaOH, extracted with diethyl ether, dried with Na2SO4, and then reacted with acetone cyanohydrin (C4HNO). The crystalline product was reacted with potassium permanganate (KMnO4) to form FPAIN, which was thoroughly characterized by two-dimensional nuclear magnetic resonance (2D NMR), infrared spectrometry (IR), high resolution mass spectrometry (HRMS), and gas chromatography mass spectrometry (GC-MS).