ISSN:
0947-3440
Keywords:
Hetero Diels-Alder reaction
;
Water chemistry
;
Solvent effects
;
Cosolvent effects
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The adduct of the Diels-Alder reaction of nitrosobenzene with cyclopentadiene is not stable in solution. The equilibrium constant for the reaction depends strongly on the medium and water induces a spectacular shift to the adduct. Comparison with the bimolecular addition of nitrosobenzene to 1,3-cyclohexadiene enables separation of the effect of the aqueous medium on the rate constants for the forward and reverse reaction. In water, the former reaction is accelerated and the latter is retarded. The deceleration of the retro reaction in water is due to hydrogen-bond stabilization of the adduct. The influence of cosolvents and micelles on the cycloreversion is discussed.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970607
Permalink
