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Chemistry of the Highly Strained Alkene Perfluorobicyclo[2.2.0]hex‐1(4)‐ene
Author(s) -
Junk Christopher P.,
He Yigang,
Zhang Yin,
Smith Joshua R.,
Dixon David A.,
Vasiliu Monica,
Lemal David M.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800058
Subject(s) - chemistry , cycloaddition , alkene , fluorocarbon , reactivity (psychology) , propellane , ene reaction , ring strain , nucleophile , fluorine , nucleophilic substitution , ring (chemistry) , photochemistry , double bond , bicyclic molecule , computational chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Several varieties of cycloaddition as well as nucleophilic and free radical addition to the highly reactive central bond of the title fluorocarbon ( 1 ) are described. [2 + 2] Cycloaddition to 1 has made available four of the five known representatives of the [2.2.2]propellane ring system, which are rare because of their extreme strain (in the absence of fluorine substitution) and high reactivity. Two of these, a propellanone and a propellene, are first reported here. Quantum mechanical calculations have shed light on many of these transformations.