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Benzvalene—Properties and Synthetic Potential
Author(s) -
Christl Manfred
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198105291
Subject(s) - double bond , bifunctional , reactivity (psychology) , chemistry , ring strain , butane , valence (chemistry) , organic synthesis , bicyclic molecule , ring (chemistry) , valence bond theory , combinatorial chemistry , computational chemistry , organic chemistry , molecule , catalysis , molecular orbital , medicine , alternative medicine , pathology
Today, thanks to the versatile synthesis developed by Katz et al. , benzvalene is not only the most extensively studied valence isomer of benezene but also one of the most easily synthesized bicyclo[1.1.0]butane derivatives. The double bond in this highly strained hydrocarbon is particulary reactive owing to interactions between the σ system and the double bond. Benzvalene is one of the most reactive olefins toward electron deficient substrates. Furthermore, the compound is bifunctional, since after addition to the π system the ring strain of the σ system provides the driving force for rearrangement or further addition reactions. This paper summarizes the spectroscopic properties and the reactivity of benzvalene. In order to demonstrate the importance of benzvalene and its derivatives as building blocks in organic synthesis the chemistry of compounds arising from benzvalene is also discussed. The article concludes with a summary of substituted benzvalenes.