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10,10′‐Bi(trispiro[2.0.2.0.2.1]decylidene): a Highly Nucleophilic Olefinic Hydrocarbon
Author(s) -
Wenck Horst,
de Meijere Armin,
Gerson Fabian,
Gleiter Rolf
Publication year - 1986
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.198603351
Subject(s) - heteroatom , chemistry , olefin fiber , nucleophile , hydrocarbon , double bond , ionization , nucleophilic addition , medicinal chemistry , ionization energy , photochemistry , stereochemistry , organic chemistry , catalysis , ring (chemistry) , ion
The title compound 1 is a record olefin in more ways than one. Not only the four α‐but also the two β‐spirocyclopropane groups exert a donor effect on the double bond. The π‐ionization potential of 7.3 eV and the oxidation potential of 0.74 V are the lowest values observed so far for monoolefins without heteroatom donor substituents.