Azide and fluoride exchange reactions of halodiazirines

…, DP Cox, DZ Denny, K Krogh-Jespersen

Index: Moss, Robert A.; Terpinski, Jacek; Cox, D. Phillip; Denneey, Dorothy Z.; Krogh-Jespersen, Karsten Journal of the American Chemical Society, 1985 , vol. 107, # 9 p. 2743 - 2748

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Citation Number: 71

Abstract

Abstract: Reactions of 3-aryl-3-bromodiazirines (11) with molten tetrabutylammonium fluoride at 25 OC provide 65-74% isolated yields of the novel corresponding 3-aryl-3- fluorodiazirines (12). Related reactions of 11 with tetrabutylammonium azide afford high yields of aryl nitriles. The latter reactions are believed to proceed through unstable intermediate 3-aryl-3-azidodiazirines (7). These reactions involve rate-determining ...

~87%

~18%

~68%

~85%

~75%

~74%

~32%

~72%

~19%

~91%

~64%

~38%

~89%

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