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Synthetic Chemistry of Quadricyclane

[ Vol. 3 , Issue. 2 ]

Author(s):

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

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.

Keywords:

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

Affiliation:

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



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