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Carbanion‐Induced Skeletal‐Rearrangements: From the Dibenzo[ a,e ] cyclooctene to the Indeno[2,1‐ a ]indene Framework
Author(s) -
Hellwinkel Dieter,
Hasselbach HansJoachim,
Lämmerzahl Frank
Publication year - 1984
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.198407051
Subject(s) - indene , chemistry , carbanion , alkyl , medicinal chemistry , nucleophile , cyclooctene , nucleophilic substitution , ring (chemistry) , stereochemistry , organic chemistry , catalysis
A surprising ring contraction to give derivatives 2 and 3 of indeno[2, 1‐ a ]indene is observed in the reaction of 1 with organolithium compounds (R = alkyl, Ph; R 1 , R 2 = H, alkyl, Ph). The expected nucleophilic substitution of 1 has so far only been accomplished in one case: with CuCN, the tetracarbonitrile 1 , CN instead of Br, is formed.