Tetrahedron

Oxidative fragmentation of 1-aryl-1-cycloalkenes using cerium (IV) ammonium nitrate (CAN): some novel observations

V Nair, SB Panicker, S Thomas, V Santhi, S Mathai

Index: Nair, Vijay; Panicker, Sreeletha B; Thomas, Siji; Santhi; Mathai, Sindhu Tetrahedron, 2002 , vol. 58, # 16 p. 3229 - 3234

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Citation Number: 8

Abstract

1-Phenyl-1-cycloalkenes undergo oxidative fragmentation in presence of CAN in methanol, affording 1, n-dicarbonyl compounds as the major products along with 1, 2- dimethoxycycloalkanes. The reaction under deoxygenated conditions afforded the latter in good yields. In the presence of azide ion, fragmentation leading to the corresponding cyanoketones was observed whereas with sulfinate only the 1-methoxy-2-sulfonyl ...