Title: Synthetic Chemistry of Quadricyclane
Volume: 3
Issue: 2
Author(s): Viacheslav A. Petrov and Nikolai V. Vasil'ev
Affiliation:
Keywords:
Quadricyclane, thermal cycloaddition reactions, photochemical cycloaddition reactions, electrophilic reactions, lithiation of C-H bond, oxidation, reduction
Abstract: This articale is the first attempt to review chemical transformation of one most interesting synthon among strained, saturated hydrocarbons - tetracyclo[3.2.0.02,704,6]heptane (quadricyclane, Q), from the point of view of synthetic organic chemistry. Thermal [2+2+2] cycloaddition reactions of Q with olefins, acetylenes, carbonyl, nitrogen, sulfur containing compounds, carbenes and silenes along with cycloaddition reactions involving transition metals are reviewed in a first part. Second part of the review covers photochemical transformations, ionic reactions (electrophilic and nucleophilic), oxidation and reduction of Q.
