The invention of radical reactions. 30. diazirines as carbon radical traps. Mechanistic aspects and synthetic applications of a novel and efficient amination process

…, JC Jaszberenyi, EA Theodorakis…

Index: Barton, Derek H. R.; Jaszberenyi, Joseph Cs.; Theodorakis, Emmanouil A.; Reibenspies Journal of the American Chemical Society, 1993 , vol. 115, # 18 p. 8050 - 8059

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Citation Number: 51

Abstract

Abstract: A number of diazirines were synthesized for the purpose of exploring the addition of a carbon radical to the nitrogen-nitrogen double bond. Carbon radicals, generated from the photolysis of the 0-acyl derivatives of N-hydroxy-2-thiopyridone or via radical exchange from the corresponding organotellurides, were shown to add smoothly to the diazirines leading to imines 34. When 3-(trifluoromethyl)-3-phenyldiazirine (13) is used as the trap, ...