Journal of fluorine chemistry

Reaction of pentafluoropyridine with lithium hydrazonides; competing monosubstitution at the 2-and 4-positions

RE Banks, WJ Jondi, AE Tipping

Index: Banks, R. Eric; Jondi, Waheed J.; Tipping, Anthony E. Journal of Fluorine Chemistry, 1996 , vol. 77, # 1 p. 87 - 92

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Citation Number: 10

Abstract

Treatment of pentafluoropyridine (1) in diethyl ether with approximately 1 M equiv. of the hydrazonides Ph2C= NNHLi (3a) and Ph2C= NNLiPh (3b) under mild conditions gives good yields (62% and 83%) of 4-and 2-(Ph2C= NH) C5F4N (5a and 6a) and 4-and 2-(Ph2C= NPh) C5F4N (5b and 6b), respectively, containing unusually large amounts of 2-substituted products (5a/6a= 50: 50; 5b/6b= 65: 35). The increased ease of displacement of a 2-F ...

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