Carbanion‐Induced Skeletal‐Rearrangements: From the Dibenzo[ a,e ] cyclooctene to the Indeno[2,1‐ a ]indene Framework | Zendy

Hellwinkel Dieter | Zendy; Hasselbach HansJoachim | Zendy; Lämmerzahl Frank | Zendy

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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.

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