3, 5-Pyridyne A Heterocyclic meta-Benzyne Derivative

M Winkler, B Cakir, W Sander

Index: Winkler, Michael; Cakir, Bayram; Sander, Wolfram Journal of the American Chemical Society, 2004 , vol. 126, # 19 p. 6135 - 6149

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Citation Number: 52

Abstract

3, 5-Pyridyne (3) has been generated by flash vacuum pyrolysis of 3, 5-diiodopyridine (20) and 3, 5-dinitropyridine (21) and characterized by IR spectroscopy in cryogenic argon matrices. The aryne can clearly be distinguished from other side products by its photolability at 254 nm, inducing a rapid ring-opening presumably to (Z)-1-aza-hex-3-ene-1, 5-diyne. As byproducts of the pyrolysis, HCN and butadiyne were identified, together with traces of ...