Abstract
Abstract This rearrangement primarily a base‐promoted rearrangement of a peroxide into a ketone and an alcohol and is known as the Kornblum–DeLaMare reaction or Kornblum–DeLaMare rearrangement. Several organic and inorganic bases have been used for this rearrangement. In addition, acidic SiO 2 has recently been observed to promote the rearrangement. The study finds that the peroxides are normally obtained by 1,4‐dioxygenation of conjugated diene with singlet oxygen (O 2 ) or photo‐[2+2] cycloaddition between singlet oxygen and alkenes. For N ‐substituted 3‐vinylindoles, it is found that both the stability of endoperoxides and the reaction products depend on the N ‐ and 3‐vinyl β‐substituents. In addition, endoperoxide arising from N ‐methyl 3‐vinyl indole is sensitive to acid and will rearrange to dioxetane, which cleaves the 3‐vinyl double bond. The β‐methoxy group on 3‐vinyl moiety accelerates the endoperoxidation when the aromatic double bond is in a cis ‐configuration. This reaction has important applications in the preparation of γ‐hydroxyenones.
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