The Journal of Organic Chemistry

Preparation and acetolysis of 7-norbornadienylmethyl and (7-methylnorbornadienyl) methyl brosylates. An intramolecular retro-Diels-Alder reaction following laticyclic …

RS Bly, RK Bly, T Shibata

Index: Bly, Robert S.; Bly, Ruta K.; Shibata, Tomoo Journal of Organic Chemistry, 1983 , vol. 48, # 1 p. 101 - 111

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Citation Number: 10

Abstract

The title compounds, 19-and ZO-OBs, respectively, have been prepared and their acetolysis rates and products determined. At 99.2'C the acetolysis of 19-OBs (k,= 3.63 X lo4 8-l) produces 40% unremanged acetate, 19-OAc, by direct displacement and 60% tetracyclo [3.3. 0.03~*. 04~ e]~~ t-7-yl acetate. Under identical conditions 20-OBs is 97 times as reactive (k,= 3.53 X sl) and yields 56% of approximately equal amounts of syn-and anti-l- ...