Diels-Alder reactions of pinacol alkenylboronates: An experimental and theoretical study
We have studied the Diels-Alder reactions of pinacol alkenylboronates with cyclopentadiene under two different sets of conditions: thermal heating at 170 °C in a pressure tube and with catalytic TFA (5 mol%) at 80 °C. Yields varied significantly from system to system and also for the uncatalyzed and catalyzed methodologies. Moderate to excellent exo-stereoselectivities were obtained in all cases. The theoretical study of the thermal reactions sheds some light on the intriguing substituent effects observed experimentally. A variety of substituted 5-norbornen-2-ols were easily generated by subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide. This journal is the Partner Organisations 2014.
Vallejos, Margarita M.,Grimblat, Nicolas,Pellegrinet, Silvina C.
p. 36385 - 36400
(2014/12/09)
1-PHENYLETHENOL: THE ENOL FORM OF ACETOPHENONE. PREPARATION, IONIZATION ENERGY AND THE HEAT OF FORMATION IN THE GAS PHASE
The enol form of acetophenone was generated in the gas phase and its ionization energy was determined as 8.01 +/- 0.03 eV.The heat of formation of the enol form was assessed as -46 +/- 6 kJ mol-1.The enol is destabilized against acetophenone by 41 kJ mol-1.
Turecek, Frantisek
p. 4219 - 4222
(2007/10/02)
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