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Diénamines hétérocycliques. III. Réexamen de la réaction de la base de Fischer avec le tétracyanoéthylène
Author(s) -
Hubschwerlen Christian,
Fleury JeanPierre,
Fritz Hans
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600420
Subject(s) - chemistry , tetracyanoethylene , isomerization , base (topology) , indoline , medicinal chemistry , stereochemistry , ring (chemistry) , organic chemistry , catalysis , mathematical analysis , mathematics
Heterocyclic dienamines III. A re‐examination of the reaction of Fischer 's base on tetracyanoethylene Depending on the order of addition, Fischer 's base 5 (1,3,3‐trimethyl‐2‐methylidene‐indoline) reacts 1:1 with tetracyanoethylene to give either the tricyanovinylation product 6 or the spiro compound 7 . A skeletal rearrangement of a zwitterionic intermediate can explain the formation of the spiro compound. The latter undergoes a thermal isomerization yielding by ring expansion the tetrahydroquinoléine 8 . On reaction with LiAlH 4 or CH 3 ONa 7 and 8 lead both to triazatetracycles. All structures are assigned on the basis of spectral data.