Tetrahedron

Photoinduced molecular transformations. Part 154. On the mechanism of the formation of the 5-iodopentyl formate in the photolysis of cyclopentanol hypoiodite in …

H Suginome, H Senboku

Index: Suginome, Hiroshi; Senboku, Hisanori Tetrahedron, 1994 , vol. 50, # 46 p. 13101 - 13112

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Abstract

18O-labelling experiments established that the formation of 5-iodopentyl formate in the photolysis of cyclopentanol hypoiodite in the presence of excess mercury (II) oxide-iodine in benzene involves the following pathway: a) a β-scission of a cyclopentyloxy radical to rearrange to a primary 5-oxopentyl radical, which generates the corresponding carbocation by a metal ion-assisted one-electron oxidation; b) an intramolecular addition of the 5- ...