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Synthetic Chemistry of Quadricyclane

[ Vol. 3 , Issue. 2 ]


Viacheslav A. Petrov and Nikolai V. Vasil'ev   Pages 215 - 259 ( 45 )


This articale is the first attempt to review chemical transformation of one most interesting synthon among strained, saturated hydrocarbons - tetracyclo[,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.


Quadricyclane, thermal cycloaddition reactions, photochemical cycloaddition reactions, electrophilic reactions, lithiation of C-H bond, oxidation, reduction


DuPont Central Researchand Development Experimental Station, P.O. Box 0328, Wilmington DE19880-0328, USA.

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