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Über den Einfluss der p K a * ‐Werte von Anilinen auf die Bildung und Folgereaktionen von substituierten Butadienen aus Cumalinsäure‐methylester
Author(s) -
Kvita Vratislav,
Sauter Hanspeter,
Rihs Grete
Publication year - 1985
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.19850680608
Subject(s) - chemistry , bicyclic molecule , reactivity (psychology) , aniline , medicinal chemistry , intramolecular force , amine gas treating , diene , intramolecular reaction , stereochemistry , organic chemistry , medicine , natural rubber , alternative medicine , pathology
The Influence of Aniline p K a *Values on the Formation and Reactivity of Substituted Butadienes from Methyl Coumalate The product of the reaction between 2 equiv. of methyl coumalate ( 1 ) and 1 equiv. of a substituted aromatic amine depends on the p K a *value of the latter. Aromatic amines with p K a *values between 1.05 and 2.8 produce bicyclic lactones 4 , whereas those with higher p K a *values also give 2‐azabicyclo[3.3.1]nona‐3,7‐diene‐9‐carboxylic acids 9 . The latter, products of the intramolecular Diels ‐ Alder reaction 8 → 9 , may in certain cases even prevail.