Photochemistry of nitrogen heterocycles. Dewar pyridine and its intermediacy in photoreduction and photohydration of pyridine

KE Wilzbach, DJ Rausch

Index: Wilzbach,K.E.; Rausch,D.J. Journal of the American Chemical Society, 1970 , vol. 92, p. 2178 - 2179

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Citation Number: 127

Abstract

We wish to report (1) that photoisomerization of pyridine to a Dewar pyridine, 2-azabicyclo [2.2. 0] hexa-2, 5-diene (I), occurs in the liquid phase at 2537 A;(2) that photoreduction of pyridine occurs in aqueous sodium borohydride, yielding 2-azabicyclo [2.2. 0] hex-5-ene (11), and (3) that I is an intermediate in the formation of 11, as well as in the photohydrationZ of pyridine to 5-amino-2, 4-pentadienal (111). The Dewar pyridine, which is the first ...