ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The Influence of Aniline pKa* Values on the Formation and Reactivity of Substituted Butadienes from Methyl CoumalateThe product of the reaction between 2 equiv. of methyl coumalate (1) and 1 equiv. of a substituted aromatic amine depends on the pKa* value of the latter. Aromatic amines with pKa* values between 1.05 and 2.8 produce bicyclic lactones 4, whereas those with higher pKa* 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.
Additional Material:
5 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680608
Permalink