Study of very reactive tautomeric phenol dienones as dienes in Diels-Alder reactions.
Masked ortho-benzoquinones are very reactive as diene partners in Diels-Alder reactions. Careful exploration of the orbital factors that govern their surprising behavior shows that their LUMO is almost as electron demanding as that of o-benzoquinone itself. Methyl substituents at either end of their diene system influence the activation energy through modification of the reaction pathway being more or less asynchronous.
Dory
Yves L
YL
Département de Chimie, Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, 3001 12e Avenue nord, Sherbrooke (Québec) J1H 5N4, Canada. yves.dory@usherbrooke.ca
Roy
Andrée-Lucie
AL
Soucy
Pierre
P
Deslongchamps
Pierre
P
D000475:Alkenes / Q000737:chemistry; D016227:Benzoquinones / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
D000475:Alkenes; D016227:Benzoquinones; D007659:Ketones; D010636:Phenols