The Journal of organic chemistry

Photochemistry of phenyl-substituted 1-methylpyrazoles

JW Pavlik, N Kebede

Index: Pavlik, James W.; Kebede, Naod Journal of Organic Chemistry, 1997 , vol. 62, # 24 p. 8325 - 8334

Full Text: HTML

Citation Number: 25

Abstract

Direct irradiation of 1-methyl-4-phenylpyrazole (2) in methanol results in regiospecific phototransposition to 1-methyl-4-phenylimidazole (4) and in photocleavage to (E)/(Z)-3-(N- methylamino)-2-phenylpropenenitrile (5) and (E)/(Z)-2-(N-methylamino)-1-phenylethenyl isocyanide (6). Deuterium labeling confirms that the phototransposition occurs via the P4 permutation pathway. Separate experiments show that 5 and 6 undergo (Z)→(E) ...