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Reactions of Electron‐Rich Olefins
Author(s) -
Hoffmann R. W.
Publication year - 1968
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.196807541
Subject(s) - tetracyanoethylene , electrophile , enol , chemistry , reactivity (psychology) , electron , photochemistry , organic chemistry , medicinal chemistry , catalysis , physics , medicine , alternative medicine , pathology , quantum mechanics
Olefins are normally preferentially attacked by electrophiles. This trend is strengthened in enol ethers and enamines, and is particularly pronounced in tetramethoxyethylene and in tetraaminoethylenes. These electron‐rich olefins are accordingly also excellent reducing agents. In their reactivity, therefore, they behave as counterparts of tetracyanoethylene. This compound shares with the electron‐rich olefins a strong tendency to undergo cycloadditions, the electron‐rich olefins adding particularly readily to electrophiles.