Synthetic Chemistry of Quadricyclane

Authors: Petrov, Viacheslav A.; Vasil'ev, Nikolai V.

Source: Current Organic Synthesis, Volume 3, Number 2, May 2006 , pp. 215-259(45)

Publisher: Bentham Science Publishers

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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

Document Type: Research article

Affiliations: 1: DuPont Central Research and Development Experimental Station, P.O. Box 0328, Wilmington DE 19880-0328, USA.

Publication date: 2006-05-01

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Current Organic Synthesis publishes in-depth reviews on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.